A Cobalt-Catalyzed Enantioconvergent Radical Negishi C(sp<sup>3</sup>)–C(sp<sup>2</sup>) Cross-Coupling with Chiral Multidentate <i>N</i>,<i>N</i>,<i>P</i>-Ligand
Zhuang Li, Xian-Yan Cheng, Ning‐Yuan Yang, Ji‐Jun Chen, Wenyue Tang, Jun-Qian Bian, Yong‐Feng Cheng, Zhong‐Liang Li, Qiang‐Shuai Gu, Xin‐Yuan Liu
Abstract
A cobalt-catalyzed enantioconvergent radical Negishi C(sp3)–C(sp2) cross-coupling of racemic benzyl chlorides with arylzinc reagents has been developed in good yield with moderate enantioselectivities. This strategy provides an expedient access toward a range of enantioenriched 1,1-diarylmethanes. Key to this discovery is the utilization of a chiral multidentate anionic N,N,P-ligand to strongly coordinate with the cobalt catalyst and tune its chiral environment, thus achieving the enantiocontrol over the highly reactive prochiral alkyl radical species.
Topics & Concepts
ChemistryDenticityNegishi couplingLigand (biochemistry)Yield (engineering)CobaltCatalysisMedicinal chemistryAlkylReagentCombinatorial chemistryStereochemistryOrganic chemistryMetalMaterials scienceBiochemistryMetallurgyReceptorCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques