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Sequential Hydrocarbon Functionalization:  Allylic C−H Oxidation/Vinylic C−H Arylation

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journal contribution
posted on 29.11.2006, 00:00 by Jared H. Delcamp, M. Christina White
A Pd(II)/sulfoxide-catalyzed sequential allylic C−H oxidation/vinylic C−H arylation of α-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 α-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 °C).