B(C6F5)3-Catalyzed hydrometalation of alkynes

ORGN 433

Todd Schwier, tschwi1@uic.edu and Vladimir Gevorgyan, vlad@uic.edu. Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Room 4500, Chicago, IL 60607-7061
An efficient method for the trans-hydrometalation of simple alkynes with silanes, germanes, and stannanes in the presence of a catalytic amount of the Lewis acid, B(C6F5)3, has been developed. Additionally, the first examples of cis-selective Lewis acid-catalyzed hydrogermylation of activated alkynes has been demonstrated. This set of methodologies allows for easy access to stereodefined vinyl metal species in high yields. The scope and limitations of this protocol will be demonstrated and the mechanisms will be discussed.

 

Modern Acetylene Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006