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Site-Selective Pyridylic C−H Functionalization by Photocatalytic Radical Cascades

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Title
Site-Selective Pyridylic C−H Functionalization by Photocatalytic Radical Cascades
Author(s)
Myojeong Kim; Euna You; Jieun Kim; Sungwoo Hong
Publication Date
2022-07
Journal
Angewandte Chemie - International Edition, v.61, no.29
Publisher
John Wiley and Sons Inc
Abstract
An efficient pyridylic C(sp3)−H functionalization has been developed through photocatalytic radical-mediated fluoroalkylation or cascade reactions. This method is enabled by the reversible formation of alkylidene dihydropyridine intermediates via the facile enolate formation of C4-alkyl N-amidopyridinium salts in the absence of an external base, thereby establishing the conditions necessary for subsequent intermolecular radical trapping. Rapid structural diversification of the pyridylic site can be achieved through photocatalytic multicomponent cascade reactions involving alkene trifluoromethylation, SO2-reincorporation, and sulfonyl radical addition. This operationally simple method features a broad substrate scope and high chemoselectivity and offers a unique approach for the rational modification of the heterobenzylic C−H bonds of pyridines and quinolines with uniform site-selective control. Furthermore, experimental and theoretical studies were performed to elucidate the reaction mechanism.
URI
https://pr.ibs.re.kr/handle/8788114/12137
DOI
10.1002/anie.202204217
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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