Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation.
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).
Delcamp
Jared H
JH
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
White
M Christina
MC
D000475:Alkenes / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis*; D004952:Esters / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D000475:Alkenes; D000498:Allyl Compounds; D004952:Esters; D020005:Propanols; D014753:Vinyl Compounds; C006463:allyl alcohol; D010165:Palladium