Efficient Nickel Precatalysts for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides and Arylboronic Acids Under Mild Conditions

被引：0

作者：

John, Morgan E. ^{[1
]}

Nutt, Michael J. ^{[1
]}

Offer, Josephine E. ^{[1
]}

Duczynski, Jeremy A. ^{[1
]}

Yamazaki, Ken ^{[2
]}

Miura, Tomoya ^{[2
]}

Moggach, Stephen A. ^{[1
]}

Koutsantonis, George A. ^{[1
]}

Dorta, Reto ^{[1
]}

Stewart, Scott G. ^{[1
]}

机构：

[1] Univ Western Australia, Sch Mol Sci, M310,35 Stirling Highway, Crawley, WA 6009, Australia

[2] Okayama Univ, Div Appl Chem, Tsushima, Okayama 7008530, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2025年

基金：

澳大利亚研究理事会;

关键词：

Air Stable; Aryl Chlorides; Boronic Acids; Nickel Catalysis; Room Temperature; Suzuki-Miyaura Cross-Coupling; CATALYTIC C-C; COMPLEXES SYNTHESIS; BENZYL CHLORIDES; LIGATION STATE; PHOSPHINE; REACTIVITY; LIGANDS; HALIDES; NI(II); ELECTROPHILES;

D O I：

10.1002/anie.202504108

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis and catalytic properties of Ni(II) complexes with the general formula Ni(NHC)[P(OR)3](Ar)Cl are described. These complexes are air-stable and extremely effective precatalysts in the Suzuki-Miyaura cross-coupling reaction. The reaction protocols described allow for the cross-coupling of aryl chlorides and arylboronic acids, employing low catalytic loading, to deliver a large variety of functionalized biaryl compounds. For the coupling of aryl chlorides with N-heterocyclic boronic acids, TBAF was used as an additive to afford nitrogen-containing biaryl products. Overall, these reaction protocols operate at room or mild temperatures and can be applied to a variety of electronically and sterically differentiated coupling partners. Fundamental insights into the mechanism of this reaction, including the proposed formation of the catalytically active Ni(NHC)[P(Oi-Pr)3] and resting state species, are also reported.

引用

页数：11

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