Visible-Light-Induced Intramolecular C(sp(2))-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway

Yipin Zhang; Xunqing Dong; Yanan Wu; Guigen Li; Hongjian Lu

doi:10.1021/acs.orglett.8b01980

Visible-Light-Induced Intramolecular C(sp(2))-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway

Yipin Zhang, Xunqing Dong, Yanan Wu, Guigen Li, Hongjian Lu

Chemistry and Biochemistry

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Abstract

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 ≈ C(sp²)-H amination ≫ C(sp³)-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.

Original language	English
Pages (from-to)	4838-4842
Number of pages	5
Journal	Default journal
Volume	20
Issue number	16
DOIs	https://doi.org/10.1021/acs.orglett.8b01980
State	Published - Aug 17 2018

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title = "Visible-Light-Induced Intramolecular C(sp(2))-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway",

abstract = "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 ≈ C(sp2)-H amination ≫ C(sp3)-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.",

author = "Yipin Zhang and Xunqing Dong and Yanan Wu and Guigen Li and Hongjian Lu",

note = "Funding Information: We acknowledge financial support from the National Natural Science Foundation of China (21472085, 21332005, 21672100) and the Fundamental Research Funds for the Central Universities (020514380131). Publisher Copyright: {\textcopyright} Copyright 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b01980",

language = "English",

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T1 - Visible-Light-Induced Intramolecular C(sp(2))-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway

AU - Zhang, Yipin

AU - Dong, Xunqing

AU - Wu, Yanan

AU - Li, Guigen

AU - Lu, Hongjian

N1 - Funding Information: We acknowledge financial support from the National Natural Science Foundation of China (21472085, 21332005, 21672100) and the Fundamental Research Funds for the Central Universities (020514380131). Publisher Copyright: © Copyright 2018 American Chemical Society.

PY - 2018/8/17

Y1 - 2018/8/17

N2 - 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 ≈ C(sp2)-H amination ≫ C(sp3)-H amination was observed, which may be instructive in the development of an understanding of visible-light-induced triplet nitrene transformation reactions.

AB - 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 ≈ C(sp2)-H amination ≫ C(sp3)-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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U2 - 10.1021/acs.orglett.8b01980

DO - 10.1021/acs.orglett.8b01980

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Visible-Light-Induced Intramolecular C(sp(2))-H Amination and Aziridination of Azidoformates via a Triplet Nitrene Pathway

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