Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 32, Pages 8051-8055Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801746
Keywords
C-H activation; cyanation; late-stage functionalization; phosphoric acid; photoredox catalysis
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Funding
- JSPS
- TOBE MAKI Scholarship Foundation
- JSPS KAKENHI [JP16H01007, JP17H06442]
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Inspired by the reaction mechanism of photo-induced DNA cleavage in nature, a C(sp(3))-H cyanation reaction promoted by visible-light photoredox/phosphate hybrid catalysis was developed. Phosphate radicals, generated by one-electron photooxidation of phosphate salt, functioned as a hydrogen-atom-transfer catalyst to produce nucleophilic carbon radicals from C(sp(3))-H bonds with a high bond-dissociation energy. The resulting carbon radicals were trapped by a cyano radical source (TsCN) to produce the C-H cyanation products. Due to the high functional-group tolerance and versatility of the cyano group, the reaction will be useful for realizing streamlined building block syntheses and late-stage functionalization of drug-like molecules.
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