Synthesis of complex allylic esters via C-H oxidation vs C-C Bond formation

Nicolaas A. Vermeulen, Jared H. Delcamp, M. Christina White

Research output: Contribution to journalArticlepeer-review

Abstract

A highly general, predictably selective C-H oxidation method for the direct, catalytic synthesis of complex allylic esters is introduced. This Pd(II)/sulfoxide-catalyzed method allows a wide range of complex aryl and alkyl carboxylic acids to couple directly with terminal olefins to furnish (E)-allylic esters in synthetically useful yields and selectivities (16 examples, E/Z ≤ 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of constructing allylic esters via C-H oxidation vs C-C bond-forming methods are evaluated and discussed in four case studies.

Original languageEnglish (US)
Pages (from-to)11323-11328
Number of pages6
JournalJournal of the American Chemical Society
Volume132
Issue number32
DOIs
StatePublished - Aug 18 2010

ASJC Scopus subject areas

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

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