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Ligand Effects on the Stereochemical Outcome of Suzuki-Miyaura Couplings

Guo-Ping Lu, Karl R. Voigtritter, Chun Cai and Bruce H. Lipshutz*

*Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States, Email: lipshutzchem.ucsb.edu

G.-P. Lu, K. R. Voigtritter, C. Cai, B. H. Lipshutz, J. Org. Chem., 2012, 77, 3700-3703.

DOI: 10.1021/jo300437t (free Supporting Information)


Abstract

In Suzuki-Miyaura coupling, Z-alkenyl halides can easily undergo Z-to-E isomerization, the extent of which is dictated mainly by the ligand on palladium. Pd(P(o-Tol)3)2 as catalyst of choice leads to the desired products under mild conditions and in high yields that, in most cases, retain their Z-olefin geometry.

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Key Words

olefination, Suzuki coupling


ID: J42-Y2012-1060