Tri-substituted �-aryl alkenoates are a common moiety in pharmaceuticals and are versatile synthetic intermediates. Generally, these �,�-disubstituted aryl alkenoates are made by olefination of ketones, cross-coupling of �-functionalized alkenoates, Heck reactions of alkenoates, or addition of aryl organometallic reagents to alkynoates. We present a new method, the reductive cross-electrophile coupling of an alkynoate with an aryl halide. Tri-substituted �-aryl alkenoate products can be readily accessed from alkynoates and aryl iodides using a simple nickel catalyst and manganese powder as the reductant in an alcohol solvent. The development and scope of this new transformation will be discussed.  

Nickel-catalyzed hydroarylation of alkynoates

248th National Meeting (2014)

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