Journal
ORGANIC LETTERS
Volume 21, Issue 3, Pages 821-825Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b04104
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Funding
- Soochow University
- National Natural Science Foundation of China [21722205]
- Project of Scientific and Technologic Infrastructure of Suzhou [SZS201708]
- Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD)
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A new approach for generation of alkoxy radical from the O-H bond of cyanohydrin promoted by visible-light photoredox catalysis is reported. The alkoxy radical triggers the successive remote HAT and intramolecular cyano migration, leading to the regioselective cyanation of remote C(sp(3))-H bonds. The reaction exhibits a broad functional group tolerance that allows many sensitive groups to remain intact under mild conditions. To demonstrate the utility of method, the ketonitrile products are converted to other synthetically valuable compounds.
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