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Selective cross-coupling of organic halides with allylic acetates.

ABSTRACT: A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieved by the use of a very hindered ligand and more reactive, branched allylic acetates.

SUBMITTER: Anka-Lufford LL

PROVIDER: S-EPMC3510762 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Selective cross-coupling of organic halides with allylic acetates.

Anka-Lufford Lukiana L LL Prinsell Michael R MR Weix Daniel J DJ

The Journal of organic chemistry 20121106 22

A general protocol for the coupling of haloarenes with a variety of allylic acetates is presented. Strengths of the method are a tolerance for electrophilic (ketone, aldehyde) and acidic (sulfonamide, trifluoroacetamide) substrates and the ability to couple with a variety of substituted allylic acetates. Secondary alkyl bromides can also be allylated under slightly modified conditions, demonstrating the generality of the approach. Finally, the coupling of a reactive vinyl halide could be achieve ...[more]

PMID: 23095043

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