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

Dmitri Chernyak, Surendra Babu Gadamsetty and Vladimir Gevorgyan

*Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, Email: vladuic.edu

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

DOI: 10.1021/ol8008705 (free Supporting Information)


Abstract

Organocopper reagents smoothly react with heterocyclic propargyl mesylates at low temperature to produce N-fused heterocycles. The copper reagent generates allenyl intermediates in situ via SN2'-substitution and copper byproducts also mediate the subsequent cycloisomerization step.

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proposed reaction pathway



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

I. V. Seregin, V. Gevorgyan, J. Am. Chem. Soc., 2006, 128, 12050-12051.


Key Words

indolizines


ID: J54-Y2008-1490