Affiliation:
1. College of Pharmacy Nanjing University of Chinese Medicine Nanjing 210023 People's Republic of China
2. State Key Laboratory and Institute of Elemento-Organic Chemistry Nankai University Tianjin 300071 People's Republic of China
Abstract
AbstractAn azidobenziodoxole (BIN3)‐mediated tunable radical reaction system for selective chlorination and bromination of tertiary and secondary C(sp3)−H bonds of alkyl substrates using haloform as the halogen donor was developed. Reactions of various substrates with BIN3 under visible light irradiation without any photo or metal catalysts gave C−H chlorinated or brominated products. These reactions are selective, and compatible with many functional groups. Mechanistic studies suggest that haloform serves as the halogen atom donor and HN3 generated in situ from the reaction of BIN3 and water relays the radical chain reaction as the hydrogen atom donor. HN3 reacts with CHX2⋅ to form CH2X2 and N3⋅, which propagates a radical chain by abstracting a hydrogen atom of the alkane substrate.
Funder
National Natural Science Foundation of China
Cited by
1 articles.
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