Synlett 2023; 34(20): 2401-2404
DOI: 10.1055/a-2060-3179
cluster
Special Issue Dedicated to Prof. Hisashi Yamamoto

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

Seiha Yamaoka
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan
,
Hiroyuki Fukuoka
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan
,
Naoki Noda
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan
,
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan
,
Masaki Horie
b   Department of Chemical Engineering, National Tsing Hua University, 101, Sec. 2, Kuang-Fu Road, Hsinchu 30013, Taiwan
,
Atsunori Mori
c   Research Center for Membrane and Film Technology, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan
a   Department of Chemical Science and Engineering, Kobe University, Rokkodai, Nada, Kobe 657-8501, Japan
› Author Affiliations
This work was supported by Kobe University Strategic International Collaborative Research Grant (Type B Fostering Joint Research).


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.

Supporting Information



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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