Journal
ORGANIC LETTERS
Volume 20, Issue 17, Pages 5523-5527Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02540
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Funding
- National Natural Science Foundation of China [21472084, 21672098, 21732003]
- Fundamental Research Funds for the Central Universities [020514380131, 020514380092]
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A unified strategy for intermolecular remote C(sp(3))-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-aryl 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(sp(3))-H and C-C cleavage and provides an efficient and versatile solution to the synthesis of gamma-vinylation of ketones and nitriles.
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