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A unified strategy for intermolecular remote C(sp3)-H and C-C vinylation of O-acyl oximes with vinyl boronic acids has been achieved. This strategy is enabled by photoreductive generation of iminyl radicals… Click to show full abstract
A unified strategy for intermolecular remote C(sp3)-H and C-C vinylation of O-acyl oximes with vinyl boronic acids has been achieved. This strategy is enabled by photoreductive generation of iminyl radicals from O-acyl oximes under irradiation by visible light. The translocated carbon-centered radicals, which are generated from the iminyl radicals through 1,5-hydrogen atom transfer or C-C cleavage, can be vinylated with vinyl boronic acids. This strategy opens up a new approach to remote functionalization via C(sp3)-H and C-C cleavage and provides an efficient and versatile solution to the synthesis of γ-vinylation of ketones and nitriles.
Journal Title: Organic letters
Year Published: 2018
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