Nickel(II) Thiocyanate Complex as a Catalyst for Cross-Coupling Reactions

Abstract

A nickel thiocyanate complex was prepared by the reaction of Ni(NCS)₂ with (2S,3S)-2,3-bis(diphenylphosphino)butane (Chiraphos) by following a method reported in the literature. The resulting nickel complex was found to be active in the polymerization reactions of 1,4-dihalobenzenes and 2-halo-3-hexylthiophenes, leading to poly-1,4-phenylenes and poly(3-hexylthiophene-2,5-diyl), respectively. The polymerization in the presence of similar catalysts containing other ligands, such as 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, or N-heterocyclic carbenes, also proceeded in a similar manner. Ni(NCS)₂ complexes also successfully catalyzed Suzuki–Miyaura couplings and Buchwald–Hartwig aminations to afford the corresponding biaryls and arylamines, respectively.

Key words

nickel catalysis - nickel thiocyanate complexes - polymerization catalysts - phosphine ligands - Suzuki–Miyaura cross-coupling - Buchwald–Hartwig amination

Publication History

Received: 09 February 2023

Accepted after revision: 22 March 2023

Accepted Manuscript online:
22 March 2023

Article published online:
14 April 2023

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