Recent Publications

Visible Light-Induced Pd-Catalyzed Alkyl-Heck Reaction of Oximes

Kvasovs, N.; Iziumchenko, V.; Palchykov, V.; Gevorgyan, V. ACS Catal. 2021, 11, 3749–3754. 

Figure 1

Contemporary Methods for Generation of Aryl Radicals

Kvasovs, N.; Gevorgyan, V. Chem. Soc. Rev. 2021, 50, 2244-2259. (Tutorial Review)

C–H Functionalization Reactions Enabled by Hydrogen Atom Transfer to Carbon-Centered Radicals

Sarkar, S.; Cheung, K. P. S.; Gevorgyan, V. Chem. Sci. 2020, 11, 12974-12993. (Perspective)

Co-Catalyzed Transannulation of Pyridotriazoles with Isothiocyanates and Xanthate Esters

Zhang, Z.; Gevorgyan, V. Org. Lett. 2020,  22, 8500–8504.

Denitrogenative Transformations of Pyridotriazoles and Related Compounds: Synthesis of N-Containing Heterocyclic Compounds and Beyond 

Yadagiri, D.; Rivas, M.; Gevorgyan, V. J. Org. Chem. 2020, 85, 11030–11046. (Perspective)

Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond

Cheung, K.P.S.; Kurandina, D.; Yata, T.; Gevorgyan, V. J. Am. Chem. Soc. 2020, 142, 9932–9937.

Visible Light‐Induced Palladium‐Catalyzed Generation of Aryl Radicals from Aryl Triflates

Ratushnyy, M.; Kvasovs, N.; Sarkar, S.; Gevorgyan, V. Angew. Chem. Int. Ed. 2020, 59, 10316-10320.

Light-Induced Metal-Free Transformations of Unactivated Pyridotriazoles

Zhang, Z.;  Yadagiri, D.; Gevorgyan, V.  Chem. Sci. 2019, 10, 8399-8404.

Transition Metal- and Light-free Directed Amination of Remote Unactivated C(sp3)–H Bonds of Alcohols

Kurandina, D.; Yadagiri, D.; Rivas, M.; Kavun, A.; Chuentragool, P.; Hayama, K.; Gevorgyan, V. J. Am. Chem. Soc. 2019141, 8104-8109.

Transition-Metal-Catalyzed Alkyl Heck-Type Reactions

Kurandina, D.; Chuentragool, P.; Gevorgyan, V. Synthesis 2019, 51, 985-1005. (Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue)

Catalysis by Visible Light Photoexcited Palladium Complexes

Chuentragool, P.; Kurandina, D.; Gevorgyan, V. Angew. Chem. Int. Ed. 2019, 58, 11586-11598. (Minireview)

Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3)–H Sites of Alcohols. 

Chuentragool, P.; Yadagiri, D.; Morita, T.; Sarkar, S.; Parasram, M.; Wang, Y.; Gevorgyan, V. Angew. Chem. Int. Ed. 2019, 58, 1794-1798.

A Mild Light-Induced Cleavage of S-O Bond of Aryl Sulfonate Esters Enables Efficient Sulfonylation of Vinylarenes

Ratushnyy, M.; Kamenova, M.; Gevorgyan, V. Chem. Sci. 2018, 9, 7193-7197.

Graphical abstract: A mild light-induced cleavage of the S–O bond of aryl sulfonate esters enables efficient sulfonylation of vinylarenes

General synthesis of pyrido[1,2-a]indoles via Pd-catalyzed cyclization of o-picolylbromoarenes

Chuentragool, P.; Li, Z.; Randle, K.; Mahchi, F.; Oshir, I.; Assaf, Sh.; Gevorgyan, V. J. Organometal. Chem. 2018, 867, 273-277. (Special Issue)

General, Mild, and Selective Method for Desaturation of Aliphatic Amines

Chuentragool, P.; Parasram, M.; Shi, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2018, 140, 2465–2468.

Pd-Catalyzed Atom Transfer Radical Cyclization at Remote Unactivated C(sp3)-H Sites Enabled by Hydrogen Atom Transfer of Hybrid Vinyl Pd-Radical Intermediates

Ratushnyy, M.; Parasram, M.; Wang, Y.; Gevorgyan, V. Angew. Chem. Int. Ed. 2018, 57, 2712-2715.

Heck Reaction of Electronically Diverse Tertiary Alkyl Halides

Kurandina, D.; Rivas, M.; Radzhabov, M.; Gevorgyan, V. Org. Lett. 2018, 20, 357-360.

General, Auxiliary-Enabled Photoinduced Pd-Catalyzed Remote Desaturation of Aliphatic Alcohols

Parasram, M.; Chuentragool, P.; Wang, Y.; Shi, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2017, 139, 14857-14860.

Visible Light-Induced Room Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes

Kurandina, D.; Parasram, M.; Gevorgyan, V. Angew. Chem. Int. Ed. 2017, 56, 14212-14216.

Visible Light-Induced Transition Metal-Catalyzed Transformations: Beyond Conventional Photosensitizers

Parasram, M.; Gevorgyan, V. Chem. Soc. Rev. 2017, 46, 6227-6240. (Tutorial Review)

Silicon-Tethered Strategies for C–H Functionalization Reactions

Parasram, M.; Gevorgyan, V. Acc. Chem. Res. 2017, 50, 2038–2053.

Synthesis of Active Hexafluoroisopropyl Benzoates through Hydrogen-Bond-Enabled Palladium(II)-Catalyzed C−H Alkoxycarbonylation Reaction

 Wang, Y.; Gevorgyan, V. Angew. Chem. Int. Ed. 2017, 56, 3191-3195.


Coinage Metals in Organic Synthesis

Echavarren, A. M.; Jiao, N.; Gevorgyan, V. Chem. Soc. Rev. 2016, 45, 4445-4447. (Editorial)

Pd-Catalyzed C-H Alkylation of Arenes Using PyrDipSi, Transformable/Removable Silicon-Tethered Directing Group

Sarkar, D.; Gevorgyan, V. Chem. Eur. J. 2016, 22, 11201-11204.

Photoinduced Formation of Hybrid Aryl Pd-Radical Species Capable of 1,5-HAT: Selective Catalytic Oxidation of Silyl Ethers into Silyl Enol Ethers

Parasram, M.; Chuentragool, P.; Sarkar, D.; Gevorgyan, V. J. Am. Chem. Soc. 2016, 138, 6340-6343.


Rhodium Thiavinyl Carbenes from 1,2,3-Thiadiazoles Enable Modular Synthesis of Multisubstituted Thiophenes

Kurandina, D.; Gevorgyan, V. Org. Lett. 2016, 18, 1804-1807. Figure 1

 Synthesis of Multisubstituted Arenes via PyrDipSi-Directed Unsymmetrical Iterative C–H Functionalizations

Sarkar, D.; Gulevich, A. V.; Melkonyan, F. S.; Gevorgyan, V. ACS. Catal. 2015, 5, 6792–6801.

Cu-Catalyzed Transannulation Reaction of Pyridotriazoles: General Access to Fused Polycyclic Indolizines

Shi, Y.; Gevorgyan, V. Chem. Commun. 2015, 51, 17166-17169.

Au-Catalyzed Pentannulation Reaction of Propargylic Esters Occurring at C(sp3)–H Site

Kazem Shiroodi, R.; Sugawara, M.; Ratushnyy, M.; Yarbrough, D. C.; Wink, D. J.; Gevorgyan, V. Org. Lett. 2015, 17, 4062–4065.

General Method for the Synthesis of Salicylic Acids from Phenols through Palladium-Catalyzed Silanol-Directed C-H Carboxylation

Wang, Y.; Gevorgyan, V. Angew. Chem. Int. Ed. 2015, 54, 2255-2259.

Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines

Kazem Shiroodi, R.; Rivera Vera, C.; Dudnik, A. S; Gevorgyan, V. Tetrahedron Lett. 2015, 56, 3251-3254.(Symposium-in-Print: Harry Wasserman)

Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines

Helan, V; Gulevich, A. V.; Gevorgyan, V. Chem. Sci. 2015, 6, 1928-1931.

Endo-Selective Pd-Catalyzed Silyl Methyl Heck Reaction

Parasram, M.; Iaroshenko, V. O.; Gevorgyan, V. J. Am. Chem. Soc. 2014, 136, 17926–17929. 

(Highlighted in ACS Selects May 2016)

Rhodium-Catalyzed NH Insertion of Pyridyl Carbenes Derived from Pyridotriazoles: A General and Efficient Approach to 2-Picolylamines and Imidazo[1,5-a]pyridines

Shi, Y.; Gulevich, A. V.; Gevorgyan, V. Angew. Chem. Int. Ed. 2014, 53, 14191-14195.

1,2-Boryl Migration Empowers Regiodivergent Synthesis of Borylated Furans

Kazem Shiroodi, R.; Koleda, O.; Gevorgyan, V. J. Am. Chem. Soc. 2014, 136, 13146-13149.

C–H activation: The road less travelled to amination

Zatolochnaya, O. V.; Gevorgyan, V. Nat. Chem. 2014, 6, 661-633. (News & Views)

Carboxylate Switch between Hydro- and Carbopalladation Pathways in Regiodivergent Dimerization of Alkynes

Zatolochnaya, O. V.; Gordeev, E. G.; Jahier, C.; Ananikov, V. P.; Gevorgyan, V. Chem. Eur. J. 2014, 20, 9578-9588.

Gold-Catalyzed 1,3-Transposition of Ynones

Kazem Shiroodi, R.; Soltani, M.; Gevorgyan, V. J. Am. Chem. Soc. 2014, 136, 9882-9885.

A New Reactivity Mode for the Diazo Group: Diastereoselective 1,3-Aminoalkylation Reaction of β-Amino-α-Diazoesters To Give Triazolines

Kuznetsov, A.; Gulevich, A.; Wink, D. J.; Gevorgyan, V. Angew. Chem. Int. Ed. 2014, 53, 9021-90125.

Conversion of 1-Alkenes into 1,4-Diols through an Auxiliary-mediated Formal Homoallylic C–H Oxidation 

Ghavtadze, N; Melkonyan, F. S.; Gulevich, A.; Huang, C.; Gevorgyan, V. Nat. Chem. 2014, 6, 122-125. (Highlighted by C&EN and Nature Chemistry)

Brönsted Acid-Catalyzed One-Pot Synthesis of Indoles from o-Aminobenzyl Alcohols and Furans.

Kuznetsov, A.; Makarov, A.; Rubtsov, A. E.; Butin, A. V.; Gevorgyan, V. J. Org. Chem. 2013, 78, 12144–12153.

Figure 1

General and Practical Carboxyl-Group-Directed Remote C-H Oxygenation Reactions of Arenes

Wang, Y.; Gulevich, A.; Gevorgyan, V. Chem. Eur. J. 2013, 19, 15836-15840.

Intramolecular Transannulation of Alkynyl Triazoles via Alkyne–Carbene Metathesis Step: Access to Fused Pyrroles 

Shi, Y.; Gevorgyan, V. Org. Lett. 2013, 15, 5394–5396.

Twofold Unsymmetrical C-H Functionalization of PyrDipSi-Substituted Arenes: A General Method for the Synthesis of Substituted meta-Halophenols 

Sarkar, D.; Melkonyan, F. S.; Gulevich, A. V.; Gevorgyan, V. Angew. Chem. Int. Ed. 2013, 52, 10800-10804.


Synthesis of Fluoro- and Perfluoroalkyl Arenes via Palladium-Catalyzed [4 + 2] Benzannulation Reaction

Zatolochnaya, O. V.; Gevorgyan, V. Org. Lett. 2013, 15, 2562-2565.

Fused Heteroaromatic Dihydrosiloles: Synthesis and Double-Fold Modification 

Kuznetsov, A.; Onishi, Y.; Inamoto, Y.; Gevorgyan, V. Org. Lett. 2013, 15, 2498-2501.

Metal-Catalyzed Double Migratory Cascade Reactions of Propargylic Esters and Phosphates

Kazem Shiroodi, R.; Gevorgyan, V. Chem. Soc. Rev. 2013, 42, 4991-5001. (Review)

Pyridine Group Assisted Addition of Diazo-Compounds to Imines in the 3-CC Reaction of 2-Aminopyridines, Aldehydes, and Diazo-Compounds

Gulevich, A. V.; Helan, V; Wink, D. J.; Gevorgyan, V. Org. Lett. 2013, 15, 956-959.

Transition Metal-Mediated Synthesis of Monocyclic Aromatic Heterocycles

Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084-3213. (Review)

Versatile Reactivity of Rhodium–Iminocarbenes Derived from N-Sulfonyl Triazoles

Gulevich, A. V.; Gevorgyan, V. Angew. Chem. Int. Ed. 2013, 52, 1371-1373. (Highlight)

Palladium-Catalyzed Carbonylative Cyclization/Arylation Cascade for 2-Aroylindolizine Synthesis 

Li, Z.; Chernyak, D.; Gevorgyan, V. Org. Lett. 2012, 14, 6056-6059.

Pd-Catalyzed Modifiable Silanol-Directed Aromatic C-H Oxygenation 

Huang, C.; Ghavtadze, N.; Godoi, B.; Gevorgyan, V. Chem. Eur. J. 2012, 18, 9789-9792.

General and Selective Head-to-Head Dimerization of Terminal Alkynes Proceeding via Hydropalladation Pathway 

Jahier, C.; Zatolochnaya, O. V.; Zvyagintsev, N. V.; Ananikov, V. P.; Gevorgyan, V. Org. Lett. 2012, 14, 2846-2849.

Beyond the Limits: Palladium-N-Heterocyclic Carbene-Based Catalytic System Enables Highly Efficient [4+2] Benzannulation Reactions

Zatolochnaya, O.; Galenko, A. V.; Gevorgyan, V. Adv. Synth. Catal. 2012, 354, 1149-1155.

Stereocontrolled 1,3-Phosphatyloxy and 1,3-Halogen Migration Relay Toward Highly Functionalized 1,3-Dienes

Kazem Shiroodi, R.; Dudnik, A. S; Gevorgyan, V. J. Am. Chem. Soc. 2012, 134, 6928-6931.

Double-Fold C-H Oxygenation of Arenes Using PyrDipSi: a General and Efficient Traceless/Modifiable Silicon Tethered Directing Group 

Gulevich, A. V.; Melkonyan, F. S.; Sarkar, D.; Gevorgyan, V. J. Am. Chem. Soc. 2012, 134, 5528–5531.

General and Practical One-Pot Synthesis of Dihydrobenzosiloles from Styrenes

Kuznetsov, A.; Gevorgyan, V. Org. Lett. 2012, 14, 914-917.

One-Pot Arylative Epoxidation of Ketones by Employing Amphoteric Bromoperfluoroarenes

Li, Z.; Gevorgyan, V. Angew. Chem. Int. Ed. 2012, 51, 1225–1227.

Transition Metal Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems

Chattopadhyay, B.; Gevorgyan, V. Angew. Chem. Int. Ed. 2012, 51, 862–872. (Minireview)

Synthesis of Fused Heterocycles via Pd-catalyzed Multiple Aromatic C-H Activation Reactions

Gulevich, A.V., Gevorgyan, V. Chem. Heterocycl. Compd. 2012, 201248, 17-20. (Highlight)

Organocopper-mediated two-component SN2′-substitution cascade towards N-fused heterocycles

Chernyak, D.; Gevorgyan, V. Chem. Heterocycl. Compd. 2011, 47, 1516-1526.

Scheme 1

 Synthesis of Catechols from Phenols via Pd-Catalyzed Silanol-Directed C–H Oxygenation 

Huang, C.; Ghavtadze, N.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 17630-17633.

Palladium-catalyzed Highly Regioselective C-3 Arylation of Imidazo[1,5-a]pyridine

Huang, C; Giokaris, A; Gevorgyan, V. Chem. Lett. 2011, 40, 1053-1054. (Special Issue)

Silanol: A Traceless Directing Group for Pd-Catalyzed o-Alkenylation of Phenols 

Huang, C.; Chattopadhyay, B.; Gevorgyan, V. J. Am. Chem. Soc. 2011, 133, 12406.

Rh-Catalyzed Transannulation of N-Tosyl-1,2,3-Triazoles with Terminal Alkynes

Chattopadhyay, Buddhadeb; Gevorgyan, V. Org. Lett. 2011, 13, 3746-3749.

The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes 

Huang, C.; Chernyak, N.; Dudnik, A. S.; Gevorgyan, V. Adv. Synth. Catal. 2011, 353, 1285.

Double Duty for Cyanogen Bromide in a Cascade Synthesis of Cyanoepoxides

Li, Z.; Gevorgyan, V. Angew. Chem. Int. Ed. 2011, 50, 2808-2810.

Palladium-Catalyzed Carbocyclization of Alkynyl Ketones Proceeding through a Carbopalladation Pathway 

Chernyak, N.; Gorelsky, S. I.; Gevorgyan, V. Angew. Chem. Int. Ed. 2011, 50, 2342.

Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine

Chernyak,N.; Tilly, D.; Li, Z.; Gevorgyan, V. ARKIVOC 2011 (V), 76-91. (Special Issue)

Transition Metal-Catalyzed Synthesis of Fused Five-Membered Aromatic Heterocycles 

Catalyzed Carbon-Heteroatom Bond Formation, (ed A. K. Yudin), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. 2010, 227-316.

Transition Metal-Catalyzed Synthesis of Monocyclic Five-Membered Aromatic Heterocycles 

Catalyzed Carbon-Heteroatom Bond Formation, (ed A. K. Yudin), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. 2010, 317-410.

On the Validity of Au-vinylidenes in the Gold-Catalyzed 1,2-Migratory Cycloisomerization of Skipped Propargylpyridines

Xia, Y; Dudnik, A. S., Li, Y.; Gevorgyan, V. Org. Lett. 2010, 12, 5538-5541.

Palladium-Catalyzed Intramolecular Carbopalladation/Cyclization Cascade: Access to Polycyclic N-Fused Heterocycles

Chernyak, D; Gevorgyan, V. Org. Lett. 2010, 12, 5558-5560.

Copper-, Silver-, and Gold Catalyzed Migratory Cycloisomerization Leading to Heterocyclic Five-Membered Rings

Dudnik, A; Chernyak, N; Gevorgyan, V. Aldrichim. Acta. 2010, 43, 37-46. (Review)

A General Strategy Toward Aromatic 1,2-Ambiphilic Synthons: Palladium-Catalyzed ortho-Halogenation of PyDipSi-Arenes

Dudnik, A.; Chernyak, N.; Huang, C.; Gevorgyan, V. Angew. Chem. Int. Ed. 2010, 49, 8729-8732.

Two-Component Approach Toward a Fully Substituted N-Fused Pyrrole Ring

Chernyak, D.; Skontos, C.; Gevorgyan, V. Org. Lett. 2010, 12, 3242-3245.

PyDipSi: A General and Easily Modifiable/Traceless Si-Tethered Directing Group for C-H Acyloxylation of Arenes 

Chernyak, N.; Dudnik, A.; Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 8270-8272.

Computation-Guided Development of Au-Catalyzed Cycloisomerizations Proceeding via 1,2-Si or 1,2-H Migrations: Regiodivergent Synthesis of Silylfurans

Dudnik, A.; Xia, Y.; Li, Y.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 7645-7655.

Synthesis of Unsymmetrical o-Biphenols and o-Binaphthols via Silicon-Tethered Pd-Catalyzed C-H Arylation

Huang, C.; Gevorgyan, V. Org. Lett. 2010, 12, 2442-2445.

Fused Tetrazoles as Azide Surrogates in Click Reaction: Efficient Synthesis of N-Heterocycle Substituted 1,2,3-Triazoles

Chattopadhyay, B.; Rivera Vera, C.; Chuprakov, S.; Gevorgyan, V. Org. Lett. 2010, 12, 2166-2169.

Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoinoles via Copper-Catalyzed Three-Component Coupling Reaction

Chernyak, D.; Chernyak, N.; Gevorgyan, V. Adv. Synth. Catal. 2010, 352, 961-966.

Formal Inverse Sonogashira Reaction: Direct Alkynylation of Arenes and Heterocycles with Alkynyl Halides 

Dudnik, A.; Gevorgyan, V. Angew. Chem. Int. Ed. 2010, 49, 2096-2098. (Highlight)

General and Efficient Copper-Catalyzed Three-Component Coupling Reaction Towards Imidazoheterocycles: One-Pot Synthesis of Alpidem and Zolpidem

Chernyak, N.; Gevorgyan, V. Angew. Chem. Int. Ed. 2010, 49, 2743-2746.

Pd-catalyzed cascade carbopalladation-annulation reaction of 3-(2-iodobenzyl)-indoles into fused 6/5/7/6- and 6/5/5/6- heterocyclic systems

Chernyak, N.; Tilly, D.; Li, Z.; Gevorgyan, V. Chem. Commun. 2010, 46,150-152. (Special Issue)

TBDPS and Br-TBDPS Protecting Groups as Efficient Aryl Group Donors in Pd-Catalyzed Arylation of Phenols and Anilines

Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2009, 131, 10844-10845.

Synthesis of Fluorenes via the Palladium-Catalyzed 5-exo-dig Annulation of o-Alkynylbiaryls

Chernyak, N.; Gevorgyan, V. Adv. Synth. Catal. 2009, 351, 1101-1114. (Special Issue)

Gold(I)-catalyzed double migration cascades toward (1E, 3E)-dienes and naphthalenes

Dudnik, A. S.; Schwier, T.; Gevorgyan, V. Tetrahedron. 2009, 65, 1859-1870. (Symposium-In-Print)

Gold(I)-Catalyzed Synthesis of (1E,3E)-dienes from propargylic esters

Dudnik, A. S.; Schwier, T.; Gevorgyan, V. J. Organomet. Chem. 2009, 694, 482-485. (Special Issue on Gold Catalysis)

Sila-Morita-Baylis-Hillman Reaction of Arylvinyl Ketones: Overcoming the Dimerization Problem

Trofimov, A.; Gevorgyan, V. Org. Lett. 2009, 11, 253-255.

Rhodium-Catalyzed Transannulation of 1,2,3-Triazoles with Nitriles

Horneff, T.; Chuprakov, S.; Chernyak N.; Gevorgyan, V. ; Fokin, V. J. Am. Chem. Soc. 2008, 130, 14972-14974.

Dual Role of Alkynyl Halides in One-Step Synthesis Of Alkynyl Epoxides

Trofimov, A.; Chernyak N.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 13538-13539.

Mechanistic Insights into the Gold-Catalyzed Cycloisomerization of Bromoallenyl Ketones: Ligand-Controlled Regioselectivity

Xia Y.; Dudnik, A. S.; Gevorgyan, V. ; Li, Y. J. Am. Chem. Soc. 2008, 130, 6940-6941.

Low Temperature Organocopper-Mediated Two-Component Cross Coupling/Cycloisomerization Approach Toward N-Fused Heterocycles

Chernyak, D.; Gadamsetty, S.; Gevorgyan, V.  Org. Lett. 2008, 10, 2307-2310.

Multisubstituted N-Fused heterocycles via transtion metal-catalyzed cycloisomerization protocols

Seregin, I.; Schammel, A.; Gevorgyan, V.  Tetrahedron. 2008, 64, 6876-6883. (Symposium-In-Print)

Exclusive 5-exo-dig Hydroarylation of o-Alkynyl Biaryls Proceeding via C−H Activation Pathway

N. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2008, 130, 5636-5637.

Gold-Catalyzed Double Migration-Benzannulation Cascade toward Naphthalenes

A. S. Dudnik, T. Schwier, V. Gevorgyan, Org. Lett. 2008, 10, 1465-1468.

Metal-Catalyzed 1,2-Shift of Diverse Migrating Groups in Allenyl Systems as a New Paradigm toward Densely Functionalized Heterocycles

A. S. Dudnik, A. W. Sromek, M. Rubina, J. T. Kim, A. V. Kel’in, V. Gevorgyan, J. Am. Chem. Soc. 2008, 130, 1440-1452.

Sila Morita-Baylis-Hillman Reaction of Cyclopropenes

S. Chuprakov, D. Malyshev, A. Trofimov, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 14868 – 14869.

Highly Diastereo- and Regioselective Transition Metal-Catalyzed Additions of Metal Hydrides and Bimetallic Species to Cyclopropenes: Easy Access to Multisubstituted Cyclopropanes

A. Trofimov, M. Rubina, M. Rubin, V. Gevorgyan, J. Org. Chem. 2007, 72, 8910-8920.

Regiodivergent Metal-Catalyzed Rearrangement of 3-Iminocyclopropenes into N-Fused Heterocycles

S. Chuprakov, V. Gevorgyan, Org. Lett. 2007, 9, 4463-4466.

Mechanistically Diverse Copper-, Silver-, and Gold-Catalyzed Acyloxy and Phosphatyloxy Migrations: Efficient Synthesis of Heterocycles via Cascade Migration/Cycloisomerization Approach

T. Schwier, A. W. Sromek, D. M. L. Yap, D. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 9868-9878.


Base- and Ligand-free Room-Temperature Synthesis of N-Fused Heteroaromatic Compounds via the Transition Metal-Catalyzed Cycloisomerization Protocol

I. V. Seregin, A. Schammel, V. Gevorgyan, Org. Lett. 2007, 9, 3433-3436.

Transition Metal Chemistry of Cyclopropenes and Cyclopropanes

M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179. (Review) 

Figure 1

Direct Palladium-Catalyzed Alkynylation of N-Fused Heterocycles

I. V. Seregin, V. Ryabova, V. Gevorgyan, J. Am. Chem. Soc. 2007, 129, 7742-7743.

Metal-Catalyzed [1,2]-Alkyl Shift in Allenyl Ketones: Synthesis of Multisubstituted Furans

A. S. Dudnik, V. Gevorgyan, Angew. Chem. Int. Ed. 2007, 46, 5195-5197.

Rh-Catalyzed Transannulation of Pyridotriazoles with Alkynes and Nitriles

S. Chuprakov, F. Hwang, V. Gevorgyan, Angew. Chem. Int. Ed. 2007, 46, 4757-4759.

Direct Pd-Catalyzed Arylation of 1,2,3-Triazoles

S. Chuprakov, N. Chernyak, A. S. Dudnik, V. Gevorgyan, Org Lett. 2007, 9, 2333-2336.

Direct transition metal-catalyzed functionalization of heteroaromatic compounds 

I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173-1193 (Review)

Graphical abstract: Direct transition metal-catalyzed functionalization of heteroaromatic compounds

1,2-Sulfur Migrations

A. W. Sromek, V. Gevorgyan, Top. Curr. Chem. 2007, 274, 77-124. (Review) 

 Gold-Catalyzed 1,2-Migration of Silicon, Tin, and Germanium en Route to C-2 Substituted Fused Pyrrole-Containing Heterocycles

Seregin, I. V.; Gevorgyan, V. J. Am. Chem. Soc. 128, 12050-12051

Chemodivergent Transformations of Alkynyl Imines

A.W. Sromek, A.L. Rheingold, D. J. Wink, V. Gevorgyan, Synlett 2006, 14, 2325-2329 (Cluster Article)

Solvent dependent photocyclization and photophysics of some 2-ethynylbiphenyls

F.D.Lewis, P.C.Karagiannis, M.C.Sajimon, K.S.Lovejoy, X. Zuo, M.Rubin, V.Gevorgyan, Photochem. Photobiol. Sci. 2006, 369-375

Graphical abstract: Solvent dependent photocyclization and photophysics of some 2-ethynylbiphenyls

Dramatic Acceleration of the Pd-Catalyzed [4+2] Benzannulation Reaction of Enynes and Diynes in the Presence of Lewis Acids and Bases: Expanded Scope and New Mechanistic Insights

M.Rubina, M.Conley V.Gevorgyan,  J. Am. Chem. Soc. 2006, 128, 5818-5827.

Recent Advances in Cyclopropene Chemistry

M. Rubin, M. Rubina, V. Gevorgyan, Synthesis 2006, 1221-1245 (Review)

Ring-Closing Photoisomerization of Some 2,6-Diarylstyrenes

F. Lewis, E. Crompton, M. Sajimon, V. Gevorgyan and M. Rubin, Photochemistry and Photobiology 2006, 82, 119-122

Competitive 1,2- and 1,5-Hydrogen Shifts Following 2-Vinylbiphenyl Photocyclization

F. D. Lewis, M. C. Sajimon, X. Zuo, M. Rubin, V. Gevorgyan,  J. Org. Chem. 2005, 70, 10447-10452.

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Trans- and Cis-Selective Lewis Acid Catalyzed Hydrogermylation of Alkynes 

Schwier, T.; Gevorgyan, V.  Org. Lett. 2005, 7, 5191-5194.

Direct Palladium-Catalyzed Arylation of Cyclopropenes 

S. Chuprakov, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc. 2005, 127, 3714-3715.

1,2-Halogen Migration in Haloallenyl Ketones: Regiodivergent Synthesis of Halofurans

A.W. Sromek, M. Rubina, V. Gevorgyan, J. Am. Chem. Soc. 2005, 127, 10500-10501.

Can Polarization of Triple Bond in Tolanes Be Deduced from 13C NMR Shifts? Re-Evaluation of Factors Affecting Regiochemistry of the Palladium-Catalyzed Hydrostannation of Alkynes 

M. Rubin, A. Trofimov, V. Gevorgyan, J. Am. Chem. Soc. 2005, 127, 10243-10249.

Selective Partial Reduction of Various Heteroaromatic Compounds with Bridgehead Nitrogen via Birch Reduction Protocol 

J. T. Kim, V. Gevorgyan, J. Org. Chem. 2005, 70, 2054-2059.

Direct Electrophilic Silylation of Terminal Alkynes 

A. A. Andreev, V. V. Konshin, N. V. Komarov, M. Rubin,  C. Brouwer, V. Gevorgyan, Org. Lett. 2004, 6, 421-424.

Highly Diastereoselective Approach toward (+/-)-Tetraponerine T6 and Analogues via the Double Cycloisomerization-Reduction of Bis-alkynylpyrimidines

J. T. Kim, J. Butt, V. Gevorgyan, J. Org. Chem. 2004, 69, 5638-5645.

B(C6F5)3-Catalyzed Allylation of Propargyl Acetates with Allylsilanes 

Schwier, T.; Rubin, M.; Gevorgyan, V. Org. Lett. 2004, 6, 1999-2001.

A Novel 1,2-Migration of Acyloxy, Phosphatyloxy, and Sulfonyloxy Groups in Allenes: Efficient Synthesis of Tri- and Tetrasubstituted Furans

Sromek, A.; Kel’in, A.; Gevorgyan, V. Angew. Chem. Int. Ed. 2004, 43, 2280-2282.

Simple Large-Scale Preparation of 3,3-Disubstituted Cyclopropenes: Easy Access to Stereodefined Cyclopropylmetals via Transition Metal-Catalyzed Hydrometallation

M. Rubin, V. Gevorgyan, Synthesis 2004, 796-800. (Practical Synthetic Procedure)

Palladium-Catalyzed Arylation and Heteroarylation of Indolizines 

Park, C.; Ryabova, V.; Seregin, I.; Sromek, A.; Gevorgyan, V.  Org. Lett. 2004, 6, 1159-1162.

Cyclopropylstannanes: Synthesis and Applications

M. Rubina, V. Gevorgyan, Tetrahedron  2004, 60, 3129-3159. (Review)

Catalytic Enantioselective Hydrostannation of Cyclopropenes

M. Rubina, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc. 2004, 126, 3688-3689.

Reduction of Carbonyl Function to a Methyl Group

G. B. Bajracharya, T. Nogami, T. Jin, K. Matsuda,  V. Gevorgyan, Y. Yamamoto, Synthesis 2004, 308-311. (Practical Synthetic Procedure)

Direct Electrophilic Silylation of Terminal Alkynes 

A. A. Andreev, V. V. Konshin, N. V. Komarov, M. Rubin,  C. Brouwer, V. Gevorgyan, Org. Lett. 2004, 6, 421-424.

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New Advances in Selected Transition Metal-Catalyzed Annulations

M. Rubin, A. W. Sromek, V. Gevorgyan, Synlett 2003, 2265-2291. (Account)

Highly Regiocontrolled Pd-Catalyzed Cross-Coupling Reaction of Terminal Alkynes and Allenylphosphine Oxides

M. Rubin, J. Markov, S. Chuprakov, D. J. Wink, V. Gevorgyan, J. Org. Chem. 2003, 68, 6251.

Catalytic Enantioselective Hydroboration of Cyclopropenes 

M. Rubina, M. Rubin, V. Gevorgyan,  J. Am. Chem. Soc. 2003, 125, 7198-7199.

1,2-Migration of the Thio Group in Allenyl Sulfides: Efficient Synthesis of 3-Thio-Substituted Furans and Pyrroles 

J. T. Kim, A. V. Kel’in, and V. Gevorgyan,  Angew. Chem. Int. Ed. 2003, 42, 98.

Double Cycloisomerization as a Novel and Expeditious Route to Tricyclic Heteroaromatic Compounds: Short and Highly Diastereoselective Synthesis of Tetraponerine T6

J. T. Kim and V. Gevorgyan, Org. Lett. 2002, 4, 4697.

IV.5. Alkynyl Substitution via Alkynylpalladation-Reductive Elimination

Handbook of Organopalladium Chemistry for Organic Synthesis, Ed. E. Nigishi, Wiley, 2002. p. 1463-1469.

IV.2.6. Carbopalladation of Alkynes Followed by Trapping with Electrophiles

V. Gevorgyan, and Y. Yamamoto.  in Handbook of Organopalladium Chemistry for Organic Synthesis, Ed. E. Nigishi, Wiley, 2002. p. 1361-1367.

Symmetry-Enforced Conformational Control of Photochemical Reactivity in 2-Vinyl-1,3-terphenyl

F. D. Lewis, X. Zuo, V. Gevorgyan, and M. Rubin, J. Am. Chem. Soc. 2002, 124, 13664-13665Abstract Image

Transition Metal-Catalyzed Hydro-, Sila-, and Stannastannation of Cyclopropenes: Stereo- and Regioselective Approach toward Multisubstituted Cyclopropyl Synthons 

M. Rubina, M. Rubin, and V. Gevorgyan, J. Am. Chem. Soc. 2002, 124, 11566-11567.

Highly Efficient B(C6F5)3-Catalyzed Hydrosilylation of Olefins 

M. Rubin, T. Schwier, and V. Gevorgyan, Org. Chem. 2002, 67, 1936.

Efficient Synthesis of 2-Mono- and 2,5-Disubstituted Furans via the CuI-Catalyzed Cycloisomerization of Alkynyl Ketones

A. V. Kel’in and V. Gevorgyan, J. Org. Chem. 2002, 67, 95.

Can Agostic Interaction Affect Regiochemistry of Carbopalladation? Reverse Regioselectivity in the Palladium-Catalyzed Dimerization of Aryl Acetylenes

M. Rubina and V. Gevorgyan, J. Am. Chem. Soc. 2001, 123, 11107.

B(C6F5)3 – Catalyzed Allylation of Secondary Benzyl Acetates with Allylsilanes 

M. Rubin and V. Gevorgyan, Org. Lett. 2001, 3, 2705.

A Novel Cu-Assisted Cycloisomerization of Alkynyl Imines: Efficient Synthesis of Pyrroles and Pyrrole-Containing Heterocycles

A. V. Kel’in, A. W. Sromek, and V. Gevorgyan, J. Am. Chem. Soc. 2001, 123, 2074.

Lewis Acid-Mediated Intramolecular Addition of Silyl Enol Ethers to Internal Unactivated Alkynes

K. Imamura, E. Yoshikawa, V. Gevorgyan, T. Sudo, N. Asao, Y. Yamamoto, Can. J. Chem. 2001, 79, 1624.

Palladium Catalyzed Highly Chemo- and Regioselective Formal [2+2+2] Sequential Cycloaddition of Alkynes: a Renaissance of the Well Known Trimerization Reaction?  

V. Gevorgyan, U. Radhakrishnan, A. Takeda, M. Rubina, M. Rubin, Y. Yamamoto, J. Org. Chem. 2001, 66, 2835.

Synthesis of Cyclophanes via an Intermolecular Pd-Catalyzed Enyne-Diyne Cross-Benzannulation Approach

V. Gevorgyan, N. Tsuboya, Y. Yamamoto, J. Org. Chem. 2001, 66, 2734.

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 A Direct Reduction of Aliphatic Aldehyde, Acyl Chloride, Ester, and Carboxylic Functions into a Methyl Group

V. Gevorgyan, M. Rubin, J.-X. Liu, Y. Yamamoto, J. Org. Chem. 2001, 66, 1672.

A Novel B(C6F5)3-Catalyzed Reduction of Alcohols and Cleavage of Aryl and Alkyl Ethers with Hydrosilanes 

V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto, J. Org. Chem. 2000, 65, 6179.

HI-Mediated Cyclization of o-Alkynylstyrenes

S. Saito, M. Homma, V. Gevorgyan, Y. Yamamoto, Chem. Lett. 2000, 722.

Palladium-Catalyzed cross-Benzannulation of Aminoenynes with Diynes. Highly Regioselective Synthesis of Polysubstituted Anilines

S. Saito, N. Uchiyama, V. Gevorgyan, Y. Yamamoto, J. Org. Chem. 2000, 65, 4338.

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Palladium-Catalyzed [2+2+1] Cyclotrimerization of Alkynes: Selective Synthesis of Fulvenes

U. Radhakrishnan, V. Gevorgyan, and Y. Yamamoto, Tetrahedron Lett. 2000, 41, 1971. 

Effective Synthesis of Aryl Ethers and Coumaranones Employing the Palladium-Catalyzed Enyne-Diyne [4+2] Cycloaddition Protocol

V. Gevorgyan, K. Tando, N. Uchiyama, and Y. Yamamoto, J. Org. Chem. 2000, 65, 568.

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A Novel Reduction of Alcohols and Ethers with a HSiEt3/Catalytic B(C6F5)3 System

V. Gevorgyan, J.-X. Liu, M. Rubin, S. Benson, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 8919.

Palladium Catalyzed [4+2] Cross-Benzannulation Reaction of Conjugated Enynes with Diynes and Triynes

V. Gevorgyan, A. Takeda, M. Homma, N. Sadayori, U. Radhakrishnan, Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 6391.

Palladium-Catalyzed Enyne-Yne [4+2] Benzannulation as a New and General Approach to Polysubstituted Benzenes

V. Gevorgyan and Y. Yamamoto, J. Organomet. Chem. 1999, 576, 232(review)

Synthesis of Indenols and Indanones via Catalytic Cyclic Vinylpalladation of Aromatic Aldehydes

V. Gevorgyan,  L. G. Quan, and Y. Yamamoto, Tetrahedron Lett. 1999, 40, 4089.

First Addition of Silyl Enol Ethers to Internal Unactivated Alkynes

K. Imamura, E. Yoshikawa, V. Gevorgyan, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 4081.

Lewis Acid Catalyzed Highly Regio- and Stereocontrolled trans-Hydrosilylation of Alkynes and Allenes

T. Sudo, N. Asao, V. Gevorgyan, Y. Yamamoto, J. Org. Chem. 1999, 64, 2494.

Intramolecular Nucleophilic Addition of Vinylpalladiums to Aryl Ketones

Long Guo Quan, Vladimir Gevorgyan, Yoshinori Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545.

An Efficient Route to 2,6-Disubstituted Styrenes via the Palladium-Catalyzed [4 + 2] Cyclodimerization of Conjugated Enynes

V. Gevorgyan, K. Tando, N. Uchiyama, Y. Yamamoto, J. Org. Chem. 1998, 63, 7022.

First Exclusive endo-dig Carbocyclization: HfCl4-Catalyzed Intramolecular Allylsilylation of Alkynes

K. Imamura, E. Yoshikawa, V. Gevorgyan, Y. Yamamoto.  J. Am. Chem. Soc. 1998, 120, 5339

Regiospecific Synthesis of Polysubstituted Phenols via  the Palladium-Catalyzed Enyne-Diyne [4+2] Cross-Benzannulation

V. Gevorgyan, L.G. Quan, Y. Yamamoto.  J. Org. Chem. 1998, 63, 1244

Synthesis of Polyether Exomethylene Paracyclophanes via  an Intramolecular Pd-Catalyzed Bis-Enyne Benzannulation Protocol

D. Weibel, V. Gevorgyan, Y. Yamamoto.J. Org. Chem. 1998, 63,1217-1220.

Hydrostannation of C-C multiple bonds with Bu3SnH prepared in situ from Bu3SnCl and Et3SiH in the presence of Lewis acid catalysts

V. Gevorgyan, J.-X. Liu, Y. Yamamoto Chem. Commun. 1998, 37.

A novel Route to Pentacoordinated Organylsilanes and -Germanes

V. Gevorgyan, L. Borisova, A. Vyater, V. Ryabova, and E. Lukevics. J. Organomet. Chem. 1997, 548, 149

The First Chemo- and Regiospecific Palladium-Catalyzed Enyne-Diyne [4+2] Intermolecular Cross-Benzannulation: An Effective Route to Polysubstituted Benzenes

V. Gevorgyan, N. Sadayori, Y. Yamamoto.  Tetrahedron Lett. 1997, 38, 8603

First Intermolecular Regiospecific Palladium Catalyzed Enyne-Diyne [4+2] Cross-Benzannulation Reaction

V. Gevorgyan, A. Takeda, Y.Yamamoto.  J. Am. Chem. Soc. 1997, 119, 11313.

Addition of Tris(trimethylsilyl)germyl Radicals to Unsaturated Compounds. An EPR and Product Study

S. Bernardony, M. Lucarini, G. F. Pedulli, L. Valgimigli, V. Gevorgyan, C. Chatgilialoglu, J. Org. Chem. 1997, 62, 8009.

Intramolecular Reaction of -Alkoxyallylstannane with Aldehyde: Origin of the Stereoselectivities

I. Kadota, M. Kawada, V. Gevorgyan, Y. Yamamoto, J. Org. Chem. 1997, 62, 7439.

Strained 6-Membered Cyclic Cumulenes as Intermediates in Dehydro Diels-Alder Cycloadditions

V. Gevorgyan, and Y. Yamamoto,  Chemtracts 1997, 10, 646.

Lewis Acid-Catalyzed trans-Allylsilylation of Unactivated Alkynes

E. Yoshikawa,  V. Gevorgyan, N. Asao, and Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 6781.

Palladium Catalyzed Addition of Carbon Pronucleophiles to Conjugated Enynes

V. Gevorgyan, C. Kadowaki, M. M. Salter, I. Kadota, S. Saito, Y. Yamamoto, Tetrahedron 1997, 53, 9097.

Regioselective Synthesis of 1,3,5-Unsymmetrically Substituted Benzenes via  the Palladium Catalyzed Cyclotrimerization of 1,3-Diynes

Takeda, A. Ohno, I. Kadota, V. Gevorgyan, and Y. Yamamoto, J. Am. Chem. Soc. 1997, 119, 4547.

Highly Regiocontrolled and Efficient Synthesis of Vinyl- and Allylstannanes via Lewis Acids and Pd-Catalyzed Hydrostannation of Allenes: Scope and Limitations

V. Gevorgyan,J-X. Liu, and Y. Yamamoto, J. Org. Chem. 1997, 62, 2963.

Reactions of Dihydrofurylsilanes With O- and N-Nucleophiles

E. Lukevics, V. Gevorgyan, L. Borisova,  Khim. Geterotsikl. Soedin. 1997, 186, (Russ.)

Organosilatranes From Reaction of Tetraorganylsilanes with Triethanolamine

V. Gevorgyan, L. Borisova, and E. Lukevics,  J. Organomet. Chem. 1997, 527, 295.

A New Palladium Catalysed Benzannulation of Conjugated Enynes

S. Saito, M. M. Salter, V. Gevorgyan, N. Tsuboya, K. Tando, Y. Yamamoto, J. Am. Chem. Soc.1996, 118, 3970.

Palladium Catalysed Addition of Certain Activated Methynes to Conjugated Enynes 

 M. M. Salter, V. Gevorgyan, S. Saito, and Y. Yamamoto, Chem. Commun. 1996, 17.