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Remote C−H Pyridylation of Hydroxamates through Direct Photoexcitation of O-Aryl Oxime Pyridinium Intermediates

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Title
Remote C−H Pyridylation of Hydroxamates through Direct Photoexcitation of O-Aryl Oxime Pyridinium Intermediates
Author(s)
Byeongseok Kweon; Changha Kim; Seonyul Kim; Sungwoo Hong
Publication Date
2021-12-13
Journal
Angewandte Chemie - International Edition, v.60, no.51, pp.26813 - 26821
Publisher
John Wiley and Sons Inc
Abstract
© 2021 Wiley-VCH GmbHHerein, we report an efficient strategy for the remote C−H pyridylation of hydroxamates with excellent ortho-selectivity by designing a new class of photon-absorbing O-aryl oxime pyridinium salts generated in situ from the corresponding pyridines and hydroxamates. When irradiated by visible light, the photoexcitation of oxime pyridinium intermediates generates iminyl radicals via the photolytic N−O bond cleavage, which does not require an external photocatalyst. The efficiency of light absorption and N−O bond cleavage of the oxime pyridinium salts can be modulated through the electronic effect of substitution on the O-aryl ring. The resultant iminyl radicals enable the installation of pyridyl rings at the γ-CN position, which yields synthetically valuable C2-substituted pyridyl derivatives. This novel synthetic approach provides significant advantages in terms of both efficiency and simplicity and exhibits broad functional group tolerance in complex settings under mild and metal-free conditions.
URI
https://pr.ibs.re.kr/handle/8788114/10844
DOI
10.1002/anie.202112364
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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