Premium
Ligand‐Facilitated Reductive Coupling of Benzyl Chlorides with Aryl Chlorides Catalyzed by Well‐Defined Heteroleptic Ni (II)‐NHC Complexes
Author(s) -
Lu Gusheng,
Li Ruipeng,
Shen Zhengwang,
Wu Qinjia,
Sun Hongmei
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5741
Subject(s) - chemistry , steric effects , aryl , ligand (biochemistry) , medicinal chemistry , catalysis , coupling reaction , reductive elimination , organic chemistry , biochemistry , alkyl , receptor
Novel heteroleptic Ni (II) complexes bearing a highly hindered yet flexible IPr * ligand, Ni (IPr * )(PPh 3 )Br 2 ( 1 ) and Ni (IPr * )(PCy 3 )Br 2 ( 2 ) (IPr * = 1,3‐bis(2,6‐bis (diphenylmethyl)‐4‐methylphenyl)imidazol‐2‐ylidene), were easily prepared in 78% and 89% yield, respectively. Both were characterized by elemental analysis and NMR spectroscopy, and 1 was subjected to X‐ray crystallography. Compared with 2 and its analogue bearing a less sterically demanding IPr ligand (IPr = 1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene), complex 1 exhibited superior catalytic activity in the magnesium‐mediated reductive coupling of benzyl chlorides with aryl chlorides, featuring outstanding tolerance of both coupling partners with steric demand. This study discloses a ligand‐facilitated reductive coupling of benzyl chlorides with aryl chlorides, which provides a new and practical synthetic tool for the synthesis of diarylmethanes.