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 50 条

[41] Microwave-Assisted Synthesis of Methylenebis(phenyl-1H-1,2,3-triazol-5-yl-1,3-thiazolidinones) as Potential Anticancer Agents
Srinivas, A.
Rajitha, S. R.
Suresh, P. D.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2023, 93 (05) : 1201 - 1209
[42] Microwave-Assisted Synthesis of Methylenebis(phenyl-1H-1,2,3-triazol-5-yl-1,3-thiazolidinones) as Potential Anticancer Agents
A. Srinivas
S. R. Rajitha
P. D. Suresh
Russian Journal of General Chemistry, 2023, 93 : 1201 - 1209
[43] Synthesis and antifungal activities of ω-[4-aryl-5-(1-phenyl-5-methyl-1,2,3-triazol-4-yl)-1,2,4-triazol-3-thio]-ω-(1H-1,2,4-triazol-1-yl)acetophenones
Chu, CH
Hui, XP
Zhang, Y
Zhang, ZY
Li, ZC
Liao, RA
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2001, 48 (01) : 121 - 125
[44] Synthesis of some novel 1-aryl-1H-1,2,3-triazole-4-carboxamides and ethyl 1-aryl-5-(1,2,3-triazol-1-yl)-1H-pyrazole-4-carboxylates
Avigliano, Marialuce
De Francesco, Debora
Brizzi, Antonella
Paolino, Marco
Corelli, Federico
Mugnaini, Claudia
ARKIVOC, 2023, : 1 - 11
[45] New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for "Click" Chemistry: Synthesis of 1,2,3-Triazole and Novel Synthesis of 1,2,3-Triazol-5-amine
Kore, Nitin
Pazdera, Pavel
CURRENT ORGANIC SYNTHESIS, 2018, 15 (04) : 552 - 565
[46] Synthesis of [5-(1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines
Pokhodylo, N. T.
Shiika, O. Ya.
Matiichuk, V. S.
Obushak, N. D.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (03) : 417 - 421
[47] Synthesis and antimicrobial activity of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives
Krolenko, Konstantin Yu.
Vlasov, Sergiy V.
Zhuravel, Irina A.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (10) : 823 - 830
[48] Synthesis of [5-(1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines
N. T. Pokhodylo
O. Ya. Shiika
V. S. Matiichuk
N. D. Obushak
Russian Journal of Organic Chemistry, 2010, 46 : 417 - 421
[49] Synthesis and antimicrobial activity of 5-(1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazole derivatives
Konstantin Yu. Krolenko
Sergiy V. Vlasov
Irina A. Zhuravel
Chemistry of Heterocyclic Compounds, 2016, 52 : 823 - 830
[50] 1,3,4-triphenyl-4,5-dihydro-1H-1,2,4-triazol-5-ylidene - Applications of a stable carbene in synthesis and catalysis
Enders, D
Breuer, K
Teles, JH
Ebel, K
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1997, 339 (04): : 397 - 399

← 1 2 3 4 5 →