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

被引：176
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
收藏
页码：2617 / 2627
页数：11
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