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Operationally Simple and Highly (E)-Styrenyl-Selective Heck Reactions of Electronically Nonbiased Olefins

Erik W. Werner and Matthew S. Sigman*

*Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, United States, Email: sigmanchem.utah.edu

E. W. Werner, M. S. Sigman, J. Am. Chem. Soc., 2011, 133, 9692-9695.

DOI: 10.1021/ja203164p (free Supporting Information)


Abstract

The use of the σ-donating DMA solvent is crucial for high selectivity in a simple, mild, and efficient Pd-catalyzed Heck reaction, that delivers (E)-styrenyl products for electronically nonbiased olefin substrates bearing a range of useful functionality in high yields. Further studies suggest that the catalyst distinguishes between β-hydrogens on the basis of their relative hydridic character.

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Key Words

Heck Reaction, Olefination


ID: J48-Y2011-1820