[(NHC)PdCl2(Aniline)] Complexes: Easily Synthesized, Highly Active Pd(II)-NHC Precatalysts for Cross-Coupling Reactions

被引：45

作者：

Xia, Qinqin ^{[1
]}

Shi, Shicheng ^{[2
]}

Gao, Pengcheng ^{[2
]}

Lalancette, Roger ^{[2
]}

Szostak, Roman ^{[3
]}

Szostak, Michal ^{[2
]}

机构：

[1] Wenzhou Med Univ, Sch Pharmaceut Sci, Wenzhou 325035, Peoples R China

[2] Rutgers State Univ, Dept Chem, Newark, NJ 07102 USA

[3] Wroclaw Univ, Dept Chem, PL-50383 Wroclaw, Poland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 21期

基金：

中国国家自然科学基金;

关键词：

HETEROCYCLIC CARBENE COMPLEXES; C-N; ARYL CHLORIDES; GENERAL-METHOD; NHC NHC; AMIDES; METAL; 21ST-CENTURY; REACTIVITY; CATALYSTS;

D O I：

10.1021/acs.joc.1c02183

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the synthesis, characterization, and reactivity of [(NHC)PdCl2 (aniline)] complexes. These well-defined, air- and moisture-stable catalysts are highly active in the Suzuki-Miyaura cross-coupling of amides by N-C(O) activation as well as in the Suzuki-Miyaura cross-coupling of esters, aryl chlorides, and Buchwald-Hartwig amination. Most crucially, this study introduces broadly available anilines as stabilizing ligands for well-defined Pd(II)-NHC catalysts. The availability of various aniline scaffolds, including structural and electronic diversity, has a significant potential in fine-tuning of challenging cross-couplings by Pd-NHCs. The parent catalyst in this class, [Pd(IPr)(AN)Cl-2], has been commercialized in collaboration with Millipore Sigma, offering broad access for reaction screening and optimization.

引用

页码：15648 / 15657

页数：10

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