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J Am Chem Soc. 2012 May 30;134(21):8778-81. doi: 10.1021/ja302457p. Epub 2012 May 18.

Stereoselective intermolecular allylic C-H trifluoroacetoxylation of functionalized alkenes.

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1
Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden.

Abstract

Pd-catalyzed allylic C-H trifluoroacetoxylation of substituted alkenes was performed using PhI(OCOCF(3))(2) as the oxidant and acyloxy source. Trifluoroacetoxylation of monosubstituted cyclopentenes and cyclohexenes proceeds with excellent regio- and diastereoselectivity. Studies with one of the possible (η(3)-allyl)Pd(II) intermediates suggest that the reaction proceeds via stereoselective formation of Pd(IV) intermediates and subsequent stereo- and regioselective reductive elimination of the product.

PMID:
22587753
DOI:
10.1021/ja302457p

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