Enantioselective Reductive <scp>Cross‐Coupling</scp> of Aryl/Alkenyl Bromides with Benzylic Chlorides <i>via</i> Photoredox/Biimidazoline Nickel Dual Catalysis
Tongtong Li, Xiaokai Cheng, Jiamin Lu, Huifeng Wang, Qun Fang, Zhan Lu
Abstract
Comprehensive Summary The asymmetric reductive arylation and alkenylation of benzylic chloride under photoredox/nickel dual catalysis using chiral biimidazoline (BiIm) ligand is reported to access 1,1‐diaryl alkanes and aryl allylic compounds with good yield as well as stereo‐ and enantioselectivities. This protocol uses more commercially available and less expensive C(sp 2 )‐Br as the electrophile coupling partner. A primary result using alkenyl chloride and alkyl chloride is also reported. Various functional groups are tolerated and the applications of this method are investigated by late‐stage functionalization and gram‐scale reaction.
Topics & Concepts
ChemistryArylElectrophileAllylic rearrangementCatalysisCombinatorial chemistryEnantioselective synthesisAlkylNickelYield (engineering)ChlorideLigand (biochemistry)Organic chemistryMedicinal chemistryMetallurgyMaterials scienceReceptorBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques