Stereospecific cross-coupling of α-(thiocarbamoyl)organostannanes with alkenyl, aryl, and heteroaryl iodides

ORGN 832

J. R. Falck, j.falck@utsouthwestern.edu, Paresh K. Patel, pareshkumar.patel@utsouthwestern.edu, and Anish Bandyopadhyay, abandyop@utsouthwestern.edu. Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Blvd, Dallas, TX 75390
Scalemic α-thiocarbamoyl-protected hydroxystannanes cross-couple with alkenyl/aryl/heteroaryl iodides in moderate to good yields using the Liebeskind catalyst (CuTC) in THF. Simple aryl iodides and 1-iodocyclohexene, two classes of electrophiles that typically react sluggishly, were also good substrates. All reactions are stereospecific with respect to the alkenyl and stannane-substituted stereocenters.

 

Metal-Mediated Reactions and Syntheses
1:00 PM-4:40 PM, Thursday, March 29, 2007 McCormick Place Lakeside -- Room E350, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007