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Photoexcited Ni<sup>II</sup>–Aryl Complex-Mediated Giese Reaction of Aryl Bromides

Xian‐Chen He, Ke-Rong Li, Jie Gao, Jianping Guan, Hong‐Bin Chen, Hao‐Yue Xiang, Kai Chen, Hua Yang

2023Organic Letters25 citationsDOI

Abstract

A Giese reaction of aryl bromides with electron-deficient alkenes was developed, enabled by a dual catalyst system containing Ni II complex and Ir III photocatalyst. This protocol could accommodate a variety of aryl bromides and electron-deficient alkenes, delivering the conjugate adducts in up to 97% yield. The utilization of photoexcited (dtbbpy)Ni II (aryl)Br intermediate as an aryl radical source allows this novel transformation of aryl halides, thus expanding the chemical space of excited nickel catalysis.

Topics & Concepts

ArylChemistryCatalysisAdductHalideYield (engineering)Medicinal chemistryNickelPhotochemistryCombinatorial chemistryOrganic chemistryMetallurgyMaterials scienceAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry
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