Issue 29, 2023

The cross-coupling reaction of organoalane reagents with 2-methylthiobenzo[d]thiazoles via C–S bond cleavage catalyzed by nickel

Abstract

A highly efficient and simple route for the synthesis of 2-substituted benzo[d]thiazoles has been developed by nickel catalyzed cross-coupling of 2-methylthiobenzo[d]thiazoles with aryl and alkenylaluminum reagents. Various 2-(hetero)aryl and 2-alkenyl substituted benzo[d]thiazoles derivatives can be obtained with 31–94% isolated yields using 4 mol% NiCl2(dppf)/4 mol% 2,2′-bipyridine as the catalyst under mild reaction conditions. The coupling reaction can be carried out smoothly whether the electron donor group or electron withdrawing group is on the aromatic ring of organic aluminum reagents or 2-methylthiobenzo[d]thiazoles derivatives. Furthermore, the broad substrate scope and the typical maintenance of vigorous efficiency on a gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[d]thiazoles derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Graphical abstract: The cross-coupling reaction of organoalane reagents with 2-methylthiobenzo[d]thiazoles via C–S bond cleavage catalyzed by nickel

Supplementary files

Article information

Article type
Paper
Submitted
03 May 2023
Accepted
16 Jun 2023
First published
19 Jun 2023

New J. Chem., 2023,47, 14078-14094

The cross-coupling reaction of organoalane reagents with 2-methylthiobenzo[d]thiazoles via C–S bond cleavage catalyzed by nickel

X. Jiang, H. Xiao, X. Jia, J. Pu, L. Han and Q. Li, New J. Chem., 2023, 47, 14078 DOI: 10.1039/D3NJ02026F

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