Flash Communication: Microwave-Assisted Synthesis of 2-Alkylphenyl-Substituted (NHC)CuCl Complexes

Abstract A base-free, microwave-assisted protocol using Cu2O and NHC·HCl salts is reported, which allows the synthesis of sterically less hindered 2-alkylphenyl-substituted (NHC)CuCl complexes, (SIMeortho)CuCl, (SIPrortho)CuCl, (IMeortho)CuCl and (IPrortho)CuCl; the use of dichloromethane in place of conventionally used tetrahydrofuran as a solvent is the key to success. Structural and NMR analyses show that 2-alkylphenyl substitution efficiently modulates the steric properties of the (NHC)CuCl complexes while largely preserving the electronic properties of the NHC ligands. This work offers a useful strategy for designing diverse NHC ligands, providing a straightforward approach to sterically tunable (NHC)CuCl complexes.

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Publication Details

Journal
Organometallics
Published
2026-09-24
DOI
https://doi.org/10.1021/acs.organomet.6c00276
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
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Flash Communication: Microwave-Assisted Synthesis of 2-Alkylphenyl-Substituted (NHC)CuCl Complexes

Takumi Tsushima, Hiroto Yoshida, Takuya Michiyuki, Masaaki Nakamoto et al.
Organometallics
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
article

Flash Communication: Microwave-Assisted Synthesis of 2-Alkylphenyl-Substituted (NHC)CuCl Complexes

Takumi Tsushima, Hiroto Yoshida, Takuya Michiyuki, Masaaki Nakamoto, Sakiha Kobayashi
article en

Abstract

Abstract A base-free, microwave-assisted protocol using Cu2O and NHC·HCl salts is reported, which allows the synthesis of sterically less hindered 2-alkylphenyl-substituted (NHC)CuCl complexes, (SIMeortho)CuCl, (SIPrortho)CuCl, (IMeortho)CuCl and (IPrortho)CuCl; the use of dichloromethane in place of conventionally used tetrahydrofuran as a solvent is the key to success. Structural and NMR analyses show that 2-alkylphenyl substitution efficiently modulates the steric properties of the (NHC)CuCl complexes while largely preserving the electronic properties of the NHC ligands. This work offers a useful strategy for designing diverse NHC ligands, providing a straightforward approach to sterically tunable (NHC)CuCl complexes.

Organometallics
Hiroshima University (JP), Hiroshima University of Economics (JP)
Openalex Percentile: Top 22%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
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Flash Communication: Microwave-Assisted Synthesis of 2-Alkylphenyl-Substituted (NHC)CuCl Complexes — Takumi Tsushima, Hiroto Yoshida, et al. · Organometallics (2026) | TGRS Research Map | TGRS