Synthesis of Highly Stable 1,3-Diaryl-1H-1,2,3-triazol-5-ylidenes and Their Applications in Ruthenium-Catalyzed Olefin Metathesis

被引：175

作者：

Bouffard, Jean ^{[2
]}

Keitz, Benjamin K. ^{[1
]}

Tonner, Ralf ^{[3
]}

Guisado-Barrios, Gregorio ^{[2
]}

Frenking, Gernot ^{[3
]}

Grubbs, Robert H. ^{[1
]}

Bertrand, Guy ^{[2
]}

机构：

[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA

[2] Univ Calif Riverside, Dept Chem, CNRS, Joint Res Chem Lab,UMI 2957, Riverside, CA 92521 USA

[3] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

ORGANOMETALLICS | 2011年 / 30卷 / 09期

基金：

美国国家科学基金会;

关键词：

N-HETEROCYCLIC CARBENES; ASYMMETRIC CONJUGATE ADDITION; CROSS-COUPLING REACTIONS; 1,3-DIAZA-2-AZONIAALLENE SALTS; PALLADIUM COMPLEXES; OXIDATIVE ADDITION; CYCLOADDITION REACTIONS; NUCLEOPHILIC-REAGENTS; TRIAZENIDE COMPLEXES; N-3-BUILDING BLOCKS;

D O I：

10.1021/om200272m

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The formal cycloaddition between 1,3-diaza-2-azoniaallene salts and alkynes or alkyne equivalents provides an efficient synthesis of 1,3-diaryl-1H-1,2,3-triazolium salts, the direct precusars of 1,2,3-triazol-5-ylidenes. These N,N-diarylated mesoionic carbenes (MICs) exhibit enhanced stability in comparison to their alkylated counterparts. Experimental and computational results confirm that these MICs act as strongly electron-donating ligands. Their increased stability allows for the preparation of ruthenium olefin metathesis catalysts that are efficient in both ring-opening and ring-closing reactions.

引用

页码：2617 / 2627

页数：11

共 142 条

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