Journal
ORGANIC LETTERS
Volume 20, Issue 16, Pages 4838-4842Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01980
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Funding
- National Natural Science Foundation of China [21472085, 21332005, 21672100]
- Fundamental Research Funds for the Central Universities [020514380131]
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Catalytic intramolecular C-H amination and aziridination reactions of o-allylphenyl azidoformates have been achieved under visible-light irradiation, providing a mild, clean, and efficient method for the synthesis of useful benzoxazolones and [5.1.0] bicyclic aziridines. Mechanistic studies suggest that a triplet nitrene acts as the reactive intermediate. The chemoselectivity of the reaction, with alkyl olefin aziridination >> electron deficient olefin aziridination approximate to C(sp(2))-H arnination >> C(sp(3))-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.
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