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Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation.

Jared H Delcamp·M Christina White
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Abstract

A Pd(II)/sulfoxide-catalyzed sequential allylic C-H oxidation/vinylic C-H arylation of alpha-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 alpha-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 degrees C).

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AlkenesAllyl CompoundsEstersOxidation-ReductionPalladiumPropanolsVinyl CompoundsJournal ArticleResearch Support, Non-U.S. Gov'tResearch Support, U.S. Gov't, Non-P.H.S.

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Jared H Delcamp, M Christina White. 2006-11-29. Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation.. https://doi.org/10.1021/ja066563d

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