Operationally Simple and Highly (E)-styrenyl-selective Heck Reactions of Electronically Nonbiased Olefins

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2011 Jun 2

PMID 21627305

Citations 33

Authors

Erik W Werner

Matthew S Sigman

Affiliations

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Abstract

Simple, mild, and efficient conditions are reported for a Pd(0)-catalyzed Heck reaction that delivers high yields and selectivity for (E)-styrenyl products using electronically nonbiased olefin substrates bearing a range of useful functionality. Preliminary mechanistic studies demonstrate that the σ-donating DMA solvent is crucial for high selectivity. Further studies suggest that the catalyst distinguishes between β-hydrogens on the basis of their relative hydridic character, in contrast to previously reported Pd(II)-catalyzed oxidative reaction conditions.

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