Premium
Nickel‐Catalyzed Coupling of Arylzinc Halides with Thioesters
Author(s) -
Gehrtz Paul H.,
Kathe Prasad,
Fleischer Ivana
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801887
Subject(s) - catalysis , reagent , halide , nickel , aryl , chemistry , acylation , substrate (aquarium) , zinc , radical , combinatorial chemistry , functional group , homogeneous , organic chemistry , thermodynamics , oceanography , geology , alkyl , polymer , physics
The Pd‐catalyzed Fukuyama reaction of thioesters with organozinc reagents is a mild, functional‐group‐tolerant method for acylation chemistry. Its Ni‐catalyzed variant might be a sustainable alternative to expensive catalytic Pd sources. We investigated the reaction of S ‐ethyl thioesters with aryl zinc halides with hetero‐ and homotopic Ni precatalysts and several ligands. The results show that both homo‐ and heterotopic species may contribute to catalysis. The substrate scope using an operationally homogeneous defined Ni complex was established. Acyl radicals are postulated as short‐lived intermediates.