Sequential hydrocarbon functionalization: Allylic C-H oxidation/vinylic C-H arylation

Jared H. Delcamp, M. Christina White

Research output: Contribution to journalArticlepeer-review

Abstract

A Pd(II)/sulfoxide-catalyzed sequential allylic C-H oxidation/vinylic C-H arylation of α-olefins to furnish E-arylated allylic esters in high regio- and E:Z selectivities (>20:1) is reported. The broad scope of this method with respect to the α-olefin, carboxylic acid, and aryl boronic acid enables the rapid assembly of densely functionalized fragments for complex molecule synthesis from cheap, abundant hydrocarbon starting materials. The Pd(II)/sulfoxide-catalyzed vinylic C-H arylation of electronically unbiased olefins with aryl boronic acids proceeds under oxidative, acidic conditions and mild temperatures (room temperature to 45 °C).

Original languageEnglish (US)
Pages (from-to)15076-15077
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number47
DOIs
StatePublished - Nov 29 2006

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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