烯烃
化学
猝灭(荧光)
组合化学
催化作用
还原消去
基质(水族馆)
光催化
多米诺骨牌
激进的
光化学
催化循环
氧化磷酸化
光催化
有机化学
荧光
海洋学
物理
地质学
量子力学
生物化学
作者
Shiyu Guo,Fan Yang,Tingting Song,Yeqin Guan,Xiang‐Ting Min,Ding‐Wei Ji,Yan‐Cheng Hu,Qing‐An Chen
标识
DOI:10.1038/s41467-021-26857-w
摘要
Abstract The Mizoroki-Heck reaction and its reductive analogue are staples of organic synthesis, but the ensuing products often lack a chemical handle for further transformation. Here we report an atom-economical cross-coupling of halopyridines and unactivated alkenes under photoredox catalysis to afford a series of alkene halopyridylation products. This protocol with mild and redox neutral conditions contributes broad substrate scope. As a complement to conventional Heck-type reaction, this radical process avoids the involvement of β -H elimination and thus useful pyridyl and halide groups could be simultaneously and regioselectively incorporated onto alkenes. The success depends on TFA-promoted domino photocatalytic oxidative quenching activation and radical-polar crossover pathway. Plausible mechanism is proposed based on mechanistic investigations. Moreover, the reserved C − X bonds of these products are beneficial for performing further synthetic elaborations.
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