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Nickel(II)‐Mediated C−S Cross‐Coupling Between Thiols and ortho ‐Substituted Arylboronic Acid
Author(s) -
Hanaya Kengo,
Ohtsu Hiroyoshi,
Kawano Masaki,
Higashibayashi Shuhei,
Sugai Takeshi
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000724
Subject(s) - chemistry , aryl , nickel , alkyl , ligand (biochemistry) , palladium , coupling reaction , rhodium , transition metal , medicinal chemistry , catalysis , base (topology) , salt (chemistry) , combinatorial chemistry , organic chemistry , polymer chemistry , mathematical analysis , biochemistry , receptor , mathematics
Abstract Herein, we report a C−S cross‐coupling reaction between alkyl thiols or aryl thiols and ortho ‐substituted arylboronic acids that proceeds in the presence of an inexpensive and ligand‐free NiCl 2 ⋅ 6H 2 O salt and N ‐methylmorpholine, a weak base, at 25 °C in air. The presence of coordinating and electron‐withdrawing groups at the ortho ‐position of the arylboronic acids played a crucial role in determining the efficiency of the reaction. X‐ray crystallographic analysis revealed that the [NiCl 2 (DMF) 2 (H 2 O) 2 ] complex was formed in‐situ . The complex is an excellent precursor of the active nickel species. The reaction offers an extremely mild and operationally convenient method to access a wide variety of alkyl aryl sulfides and diaryl sulfides without using expensive transition metals, such as palladium, gold, and rhodium, and specialized and expensive ligands.