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Communication

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

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Ilya V. Seregin and Vladimir Gevorgyan*

Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061

J. Am. Chem. Soc., 2006, 128 (37), pp 12050–12051

DOI: 10.1021/ja063278l

Publication Date (Web): August 24, 2006

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, vlad@uic.edu

Abstract

An efficient method for the synthesis of fused pyrroloheterocycles from diverse propargyl-substituted heterocycles in the presence of Au-catalyst has been developed. The cascade transformation proceeds via alkyne−vinylidene isomerization with concomitant 1,2-shift of hydrogen, silyl, and stannyl groups. Remarkably, it was also shown that previously unknown 1,2-migration of a germyl group upon alkyne−vinylidene rearrangement occurs under these reaction conditions. This method allows for mild and efficient synthesis of diverse C-2 substituted N-containing heterocycles.

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Published In Issue September 20, 2006
Received May 10, 2006

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Communication

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

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

Pt-Catalyzed Cyclization/1,2-Migration for the Synthesis of Indolizines, Pyrrolones, and Indolizinones

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

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