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
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.
see article for more examples
proposed reaction pathway
I. V. Seregin, V. Gevorgyan, J. Am. Chem. Soc., 2006, 128, 12050-12051.
A. V. Kel'in, A. W. Sromek, V. Gevorgyan, J. Am. Chem. Soc., 2001, 123, 2074-2075.
Key Words
ID: J54-Y2008-1490