Photo-induced catalytic halopyridylation of alkenes

Shi-Yu Guo, Fan Yang, Ting-Ting Song, Yu-Qing Guan, Xiang-Ting Min, Ding-Wei Ji, Yan-Cheng Hu and Qing-An Chen ()
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Shi-Yu Guo: Chinese Academy of Sciences
Fan Yang: Chinese Academy of Sciences
Ting-Ting Song: Chinese Academy of Sciences
Yu-Qing Guan: Chinese Academy of Sciences
Xiang-Ting Min: Chinese Academy of Sciences
Ding-Wei Ji: Chinese Academy of Sciences
Yan-Cheng Hu: Chinese Academy of Sciences
Qing-An Chen: Chinese Academy of Sciences

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-26857-w

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