Operationally simple and highly (E)-styrenyl-selective Heck reactions of electronically nonbiased olefins
Erik W Werner1, Matthew S Sigman
1Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
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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