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Nickel-Catalyzed Reductive Csp<sup>2</sup>–Csp<sup>3</sup> Cross Coupling Using Phosphonium Salts

Huifei Wang, Mengwan Yang, Yu‐Ting Wang, Xi Man, Xinyao Lu, Zehuai Mou, Yunjie Luo, Hongze Liang

2021Organic Letters34 citationsDOI

Abstract

A nickel-catalyzed reductive cross coupling with phosphonium salts and allylic C(sp3)–O bond electrophiles, which granted direct construction of the C(sp2)–C(sp3) bond, is successfully developed. The protocol features broad substrate scope, high-functional-group tolerance, and heterocycle compatibility. Notably, the much more challenging reductive cross coupling with heterocyclic thiazolylphosphonium salts has also been accomplished for the first time.

Topics & Concepts

PhosphoniumChemistryElectrophileNickelCatalysisReagentAllylic rearrangementCombinatorial chemistryFunctional groupMedicinal chemistryPolymer chemistryOrganic chemistryPolymerCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions
Nickel-Catalyzed Reductive Csp<sup>2</sup>–Csp<sup>3</sup> Cross Coupling Using Phosphonium Salts | Litcius