Synfacts 2008(11): 1208-1208  
DOI: 10.1055/s-0028-1083466
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Selective Chelate-Controlled Heck-Miyaura Coupling Reaction

Contributor(s): Paul Knochel, Tobias Thaler
J. H. Delcamp, A. P. Brucks, M. C. White*
University of Illinois, Urbana-Champaign, USA
Further Information

Publication History

Publication Date:
23 October 2008 (online)

Significance

A new general and highly selective protocol for an oxidative chelate-controlled Heck-Miyaura coupling has been disclosed. The reaction proceeds with remarkably high regioselectivities and with preservation of the optical purity of proximal stereocenters. No Pd-H isomerization is observed under the mild reaction conditions leading to excellent E:Z selectivities (>20:1 in all cases).