化学
烯烃
化学选择性
表面改性
光催化
三氟甲基化
光化学
磺酰
组合化学
烷基
光催化
级联
级联反应
催化作用
三氟甲基
有机化学
物理化学
色谱法
作者
Myojeong Kim,Euna You,Jieun Kim,Sungwoo Hong
标识
DOI:10.1002/anie.202204217
摘要
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.
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