Palladium-catalyzed C-CN activation for intramolecular cyanoesterification of alkynes |
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| Authors: | Rondla Naveen R Levi Samuel M Ryss Jonathan M Vanden Berg Rachel A Douglas Christopher J |
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| Institution: | Department of Chemistry, 207 Pleasant Street, SE, University of Minnesota, Minneapolis, Minnesota 55455, USA. |
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| Abstract: | Conditions for the C-CN activation and intramolecular cyanoesterification of alkynes to provide butenolides in good to excellent yields are presented. Pd catalysts, high temperatures/short reaction times (microwave irradiation), and Lewis basic solvents minimized competitive decarbonylation. Less sterically encumbered, electron-rich alkynes underwent cyanoesterification with greater ease compared to sterically encumbered, electron-deficient alkynes. The results led to the hypothesis that migratory insertion of the alkyne, rather than C-CN activation, might be the product-determining step. |
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