Gevorgyan Group – Home Page

Publications

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

    Alexander S. Dudnik, Natalia Chernyak, Chunhui Huang, Vladimir Gevorgyan*

    Angew. Chem. Int. Ed. 2010, 49, 8729–8732

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

    Dmitri Chernyak, Cathy Skontos, Vladimir Gevorgyan*

    Org. Lett. 2010, 12, 3242–3245

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

    Natalia Chernyak, Alexander S. Dudnik, Chunhui Huang, Vladimir Gevorgyan*

    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
     

    Alexander S. Dudnik†, Yuanzhi Xia‡§, Yahong Li*‡§, Vladimir Gevorgyan*†

    J. Am. Chem. Soc. 2010, 132, 7645–7655

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

    Chunhui Huang, Vladimir Gevorgyan*

    Org. Lett. 2010, 12, 2442–2445

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

    Dmitri Chernyak, Natalia Chernyak, Vladimir Gevorgyan*

    Adv. Synth. Catal. 2010, 352, 961–966

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

    Buddhadeb Chattopadhyay, Claudia I. Rivera Vera, Stepan Chuprakov, Vladimir Gevorgyan*

    Org. Lett. 2010, 12, 2166–2169

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

    Natalia Chernyak, Vladimir Gevorgyan*

    Angew. Chem. Int. Ed. 2010, 49, 2743–2746

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

    Alexander S. Dudnik, Vladimir Gevorgyan*

    Angew. Chem. Int. Ed. 2010, 49, 2096–2098

    (Highlight)

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

    Natalia Chernyak, David Tilly, Zhou Li, Vladimir Gevorgyan*

    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

    Chunhui Huang, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2009, 131, 10844–10845

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

    Natalia Chernyak, Vladimir Gevorgyan*

    Adv. Synth. Catal. 2009, 351, 1101–1114

    (Special Issue)

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

    Alexander S. Dudnik, Todd Schwier, Vladimir Gevorgyan*

    Tetrahedron. 2009, 65, 1859–1870

    (Symposium-In-Print)

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

    Alexander S. Dudnik, Todd Schwier, Vladimir Gevorgyan*

    J. Organomet. Chem. 2009, 694, 482–485

    (Special Issue on Gold Catalysis)

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

    Alexander Trofimov, Vladimir Gevorgyan*

    Org. Lett. 2009, 11, 253–255

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

    Tony Horneff†, Stepan Chuprakov†, Natalia Chernyak‡, Vladimir Gevorgyan*‡ ,Valery V. Fokin*†

    J. Am. Chem. Soc. 2008, 130, 14972–14974

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

    Alexander Trofimov, Natalia Chernyak, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2008, 130, 13538–13539

  • Multisubstituted N-Fused heterocycles via transition metal-catalyzed cycloisomerization protocols

    Ilya V. Seregin, Alex W. Schammel, Vladimir Gevorgyan*

    Tetrahedron. 2008, 64, 6876-6883

    (Symposium-In-Print)

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

    Dmitri Chernyak, Surendra Babu Gadamsetty, Vladimir Gevorgyan*

    Org. Lett. 2008, 10, 2307–2310

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

    Yuanzhi Xia†‡ ,Alexander S. Dudnik§ ,Vladimir Gevorgyan§, Yahong Li†‡

    J. Am. Chem. Soc. 2008, 130, 6940–6941

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

    Natalia Chernyak, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2008, 130, 5636-5637

  • Gold-Catalyzed Double Migration-Benzannulation Cascade toward Naphthalenes

    Alexander S. Dudnik, Todd Schwier, Vladimir 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

    Alexander S. Dudnik , Anna W. Sromek , Marina Rubina , Joseph T. Kim, Alexander V. Kel’i, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2008, 130, 1440–1452

  • Sila Morita-Baylis-Hillman Reaction of Cyclopropenes

    Stepan Chuprakov, Denis A. Malyshev, Alexander Trofimov, Vladimir 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

    Alexander Trofimov, Marina Rubinam, Michael Rubin, Vladimir Gevorgyan*

    J. Org. Chem. 2007, 72, 8910–8920

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

    Stepan Chuprakov, Vladimir Gevorgyan*

    Org. Lett. 2007, 9, 4463–4466

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

    Ilya V. Seregin, Alex W. Schammel, Vladimir Gevorgyan*

    Org. Lett. 2007, 9, 3433–3436

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

    Todd Schwier, Anna W. Sromek, Dahrika M. L. Yap, Dmitri Chernyak, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2007, 129, 9868–9878

  • Transition Metal Chemistry of Cyclopropenes and Cyclopropanes

    Michael Rubin, Marina Rubina, Vladimir Gevorgyan*

    Chem. Rev. 2007, 107, 3117–3179

    (Review) 

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

    Alexander S. Dudnik, Vladimir Gevorgyan*

    Angew. Chem. Int. Ed. 2007, 46, 5195–5197

  • Rh-Catalyzed Transannulation of Pyridotriazoles with Alkynes and Nitriles

    Stepan Chuprakov, Frank W. Hwang, Vladimir Gevorgyan*

    Angew. Chem. Int. Ed. 2007, 46, 4757–4759

  • Direct Palladium-Catalyzed Alkynylation of N-Fused Heterocycles

    Ilya V. Seregin, Victoria Ryabova, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2007, 129, 7742–7743

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

    Stepan Chuprakov, Natalia Chernyak, Alexander S. Dudnik, Vladimir Gevorgyan*

    Org Lett. 2007, 9, 2333–2336

  • Ring-Closing Photoisomerization of Some 2,6-Diarylstyrenes

    Frederick D. Lewis*, Elizabeth M. Crompton, Meledathu C. Sajimon, Vladimir Gevorgyan, Michael Rubin

    Photochemistry and Photobiology 2006, 82, 119–122

  • Direct transition metal-catalyzed functionalization of heteroaromatic compounds

    Ilya V. Seregin, Vladimir Gevorgyan*

    Chem. Soc. Rev. 2007, 36, 1173–1193

    (Review)

  • 1,2-Sulfur Migrations

    Anna W. Sromek, Vladimir Gevorgyan*

    Top. Curr. Chem. 2007, 274, 77–124

    (Review) 

  • Chemodivergent Transformations of Alkynyl Imines

    Anna W. Sromek, Arnold L. Rheingold, Donald J. Wink, Vladimir Gevorgyan*

    Synlett 2006, 14, 2325–2329

    (Cluster Article)

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

    Ilya V. Seregin, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2006, 128, 12050–12051

  • 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

    Marina Rubina, Matthew Conley, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2006, 128, 5818–5827

  • Recent Advances in Cyclopropene Chemistry

    Michael Rubin, Marina Rubina, Vladimir Gevorgyan*

    Synthesis 2006, 1221–1245

    (Review)

  • Solvent dependent photocyclization and photophysics of some 2-ethynylbiphenyls

    Frederick D. Lewis,*a   Paul C. Karagiannis,a   Meledathu C. Sajimon,a   Katherine S. Lovejoy,a   Xiaobing Zuo,a   Michael Rubinb, Vladimir Gevorgyan*b

    Photochem. Photobiol. Sci. 2006, 369–375

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

    Frederick D. Lewis, Meledathu C. Sajimon, Xiaobing Zuo, Michael Rubin, Vladimir Gevorgyan*

    J. Org. Chem. 2005, 70, 10447–10452

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

    Todd Schwier, Vladimir Gevorgyan*

    Org. Lett. 2005, 7, 5191–5194

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

    Anna W. Sromek, Marina Rubina, Vladimir 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 

    Michael Rubin, Alexander Trofimov, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2005, 127, 10243–10249

  • Direct Palladium-Catalyzed Arylation of Cyclopropenes

    Stepan Chuprakov, Michael Rubin, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2005, 127, 3714–3715

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

    Joseph T. Kim, Vladimir Gevorgyan*

    J. Org. Chem. 2005, 70, 2054–2059

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

    Joseph T. Kim, Jason Butt, Vladimir Gevorgyan*

    J. Org. Chem. 2004, 69, 5638–5645

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

    Todd Schwier, Michael Rubin, Vladimir Gevorgyan*

    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

    Anna W. Sromek, Alexander V. Kel’in, Vladimir Gevorgyan*

    Angew. Chem. Int. Ed. 2004, 43, 2280–2282

  • Cyclopropylstannanes: Synthesis and Applications

    Marina Rubina, Vladimir Gevorgyan*

    Tetrahedron 2004, 60, 3129–3159

    (Review)

  • Catalytic Enantioselective Hydrostannation of Cyclopropenes

    Marina Rubina, Michael Rubin, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2004, 126, 3688–3689

  • Palladium-Catalyzed Arylation and Heteroarylation of Indolizines

    Choul-Hong Park, Victoria Ryabova, Ilya V. Seregin, Anna W. Sromek, Vladimir Gevorgyan*

     Org. Lett. 2004, 6, 1159–1162

  • Direct Electrophilic Silylation of Terminal Alkynes 

    Aleksey A. Andreev, Valeri V. Konshin, Nikolai V. Komarov, Michael Rubin, Chad Brouwer, Vladimir Gevorgyan*

    Org. Lett. 2004, 6, 421–424

  • Direct Electrophilic Silylation of Terminal Alkynes 

    Aleksey A. Andreev, Valeri V. Konshin, Nikolai V. Komarov, Michael Rubin, Chad Brouwer, Vladimir Gevorgyan*

    Org. Lett. 2004, 6, 421–424

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

    Michael Rubin, Vladimir Gevorgyan*

    Synthesis 2004, 796–800

    (Practical Synthetic Procedure)

  • Reduction of Carbonyl Function to a Methyl Group

    Gan B. Bajracharyaa, Tsutomu Nogamia, Tienan Jina, Kumiko Matsudaa, Vladimir Gevorgyanb, Yoshinori Yamamoto*a

    Synthesis 2004, 308–311

    (Practical Synthetic Procedure)

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

    Michael Rubin, Jelena Markov, Stepan Chuprakov, Donald J. Wink, Vladimir Gevorgyan*

    J. Org. Chem. 2003, 68, 6251–6256

  • Catalytic Enantioselective Hydroboration of Cyclopropenes 

    Marina Rubina, Michael Rubin, Vladimir 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 

    Joseph T. Kim, Alexander V. Kel’in, Vladimir Gevorgyan*

    Angew. Chem. Int. Ed. 2003, 42, 98–101

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

    Joseph T. Kim, Vladimir Gevorgyan*

    Org. Lett. 2002, 4, 4697–4699

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

    Alexander V. Kel’i, Vladimir Gevorgyan*

    J. Org. Chem. 2002, 67, 95–98

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

    Frederick D. Lewis, Xiaobing Zuo, Michael Rubin, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2002, 124, 13664–13665

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

    Marina Rubina, Michael Rubin, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2002, 124, 11566–11567

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

    Vladimir Gevorgyan and Yoshinori Yamamoto

    Handbook of Organopalladium Chemistry for Organic Synthesis, Ed. E. Nigishi, Wiley, 2002. p. 1361–1367

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

    Vladimir Gevorgyan and Yoshinori Yamamoto

    Handbook of Organopalladium Chemistry for Organic Synthesis, Ed. E. Nigishi, Wiley, 2002. p. 1361–1367

  • IV.5. Alkynyl Substitution via Alkynylpalladation-Reductive Elimination

    Vladimir Gevorgyan

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

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

    Michael Rubin, Todd Schwier, Vladimir Gevorgyan*

    J. Org. Chem. 2002, 67, 1936–1940

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

     Ken-ichiro Imamura, Eiji Yoshikawa, Vladimir Gevorgyan, Tomoko Sudo, 

    Naoki Asa, Yoshinori Yamamoto*

    Can. J. Chem. 2001, 79, 1624–1631

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

    Marina Rubina, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2001, 123, 11107–11108

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

    Michael Rubin, Vladimir Gevorgyan*

    Org. Lett. 2001, 3, 2705–2707

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

    Vladimir Gevorgyan, Ukkiramapandian Radhakrishnan, Akira Takeda, Marina Rubina, Michael Rubin, Yoshinori Yamamoto*

    J. Org. Chem. 2001, 66, 2835–2841

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

    Vladimir Gevorgyan, Norie Tsuboya, Yoshinori Yamamoto*

    J. Org. Chem. 2001, 66, 2734–2746

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

    Vladimir Gevorgyan, Michael Rubin, Jian-Xiu Liu, Yoshinori Yamamoto*

    J. Org. Chem. 2001, 66, 1672–1675

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

    Alexander V. Kel’in, Anna W. Sromek, Vladimir Gevorgyan*

    J. Am. Chem. Soc. 2001, 123, 2074–2075

The University of Texas at Dallas