Litcius/Paper detail

Nickel/Photoredox‐Catalyzed Asymmetric Reductive Cross‐Coupling of Racemic α‐Chloro Esters with Aryl Iodides

Haixing Guan, Qianwen Zhang, Patrick J. Walsh, Jianyou Mao

2020Angewandte Chemie International Edition167 citationsDOI

Abstract

A unique nickel/organic photoredox co-catalyzed asymmetric reductive cross-coupling between α-chloro esters and aryl iodides is developed. This cross-electrophile coupling reaction employs an organic reductant (Hantzsch ester), whereas most reductive cross-coupling reactions use stoichiometric metals. A diverse array of valuable α-aryl esters is formed under these conditions with high enantioselectivities (up to 94 %) and good yields (up to 88 %). α-Aryl esters represent an important family of nonsteroidal anti-inflammatory drugs. This novel synergistic strategy expands the scope of Ni-catalyzed reductive asymmetric cross-coupling reactions.

Topics & Concepts

ArylNickelCatalysisChemistryCoupling (piping)Organic chemistryCombinatorial chemistryMaterials scienceMetallurgyAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry