Stereospecific cross-coupling of aryl halides with in situ generated chromium E-halovinylidenes

ORGN 446

J. R. Falck1, D. K. Barma1, Anish Bandyopadhyay1, Abhijit Kundu1, and Charles Mioskowski2. (1) Biochemistry, University of Texas Southwestern Medical Center, 5323 Harry Hines Blvd., Dallas, TX 75390, (2) Bio-Organique, Universite Louis Pasteur de Strasbourg, 74, route du Rhin, Illkirch, 67401, France
Chromium E-halovinylidenes, generated in situ from trihaloalkanes using CrCl2, stereospecifically cross couple with aryl bromides and iodides in the presence of Pd(0). This one pot transformation provides unrivaled access to tri-substituted Z-a-halostyrenes in good overall yield. The scope and limitations of this remarkable reaction will be described.

 

Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster

Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003