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Operationally simple and highly (E)-styrenyl-selective Heck reactions of electronically nonbiased olefins.

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 ?-donating DMA solvent is crucial for high selectivity. Further studies suggest that the catalyst distinguishes between ?-hydrogens on the basis of their relative hydridic character, in contrast to previously reported Pd(II)-catalyzed oxidative reaction conditions.

SUBMITTER: Werner EW

PROVIDER: S-EPMC3124000 | biostudies-literature | 2011 Jun

REPOSITORIES: biostudies-literature

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Operationally simple and highly (E)-styrenyl-selective Heck reactions of electronically nonbiased olefins.

Werner Erik W EW Sigman Matthew S MS

Journal of the American Chemical Society 20110606 25

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 pre ...[more]

PMID: 21627305

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