Literature DB >> 16089452

Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction.

David J Gorin1, Nicole R Davis, F Dean Toste.   

Abstract

Substituted pyrroles were prepared by a gold(I)-catalyzed acetylenic Schmidt reaction of homopropargyl azides. The reaction allows for regiospecific substitution at each position of the pyrrole ring under mild conditions. A mechanism in which azides serve as nucleophiles toward gold(I)-activated alkynes with subsequent gold(I)-aided expulsion of dinitrogen is proposed.

Entities:  

Year:  2005        PMID： 16089452     DOI： 10.1021/ja053804t

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  38 in total

1.  Copper-, Silver-, and Gold-Catalyzed Migratory Cycloisomerizations Leading to Heterocyclic Five-Membered Rings.

Authors:  Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Aldrichimica Acta       Date:  2010       Impact factor: 3.667

2.  Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors:  Ilya V Seregin; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2006-09-20       Impact factor: 15.419

3.  Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: synthesis of multisubstituted furans.

Authors:  Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

4.  Base- and ligand-free room-temperature synthesis of N-fused heteroaromatic compounds via the transition metal-catalyzed cycloisomerization protocol.

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2007-07-17       Impact factor: 6.005

5.  Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

Authors:  Alexander S Dudnik; Yuanzhi Xia; Yahong Li; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2010-06-09       Impact factor: 15.419

Review 6.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

7.  Gold(I)-catalyzed enantioselective [4 + 2]-cycloaddition of allene-dienes.

Authors:  Ana Z González; F Dean Toste
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

8.  Multisubstituted N-fused heterocycles via transition metal-catalyzed cycloisomerization protocols.

Authors:  Ilya V Seregin; Alex W Schammel; Vladimir Gevorgyan
Journal:  Tetrahedron       Date:  2008-07-14       Impact factor: 2.457

9.  Triflic acid controlled successive annelation of aromatic sulfonamides: An efficient one-pot synthesis of N-sulfonyl pyrroles, indoles and carbazoles.

Authors:  Mohammed Abid; Liliana Teixeira; Béla Török
Journal:  Tetrahedron Lett       Date:  2007-06-04       Impact factor: 2.415

10.  A bonding model for gold(I) carbene complexes.

Authors:  Diego Benitez; Nathan D Shapiro; Ekaterina Tkatchouk; Yiming Wang; William A Goddard; F Dean Toste
Journal:  Nat Chem       Date:  2009-09       Impact factor: 24.427
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