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

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 >or= 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".

SUBMITTER: Vermeulen NA

PROVIDER: S-EPMC3047454 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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

Vermeulen Nicolaas A NA Delcamp Jared H JH White M Christina MC

Journal of the American Chemical Society 20100801 32

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 >or= 10:1) and without the use of stoichiometric coupling reagents or unstable intermediates. Strategic advantages of cons ...[more]

PMID: 20662536

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