Ruthenium-arene complexes bearing imidazol(in)ium-2-dithiocarboxylate ligands: Evaluation of their catalytic activity in the synthesis of enol esters

被引:21
作者
Willem, Quentin [1 ]
Nicks, Francois [1 ]
Sauvage, Xavier [1 ]
Delaude, Lionel [1 ]
Demonceau, Albert [1 ]
机构
[1] Univ Liege, Lab Macromol Chem & Organ Catalysis, B-4000 Liege, Belgium
关键词
Alkynes; Carboxylic acids; Enol esters; N-Heterocyclic carbene ligands; Microwave; Ruthenium; HETEROCYCLIC CARBENE PRECURSORS; MICROWAVE-ASSISTED SYNTHESIS; OPENING METATHESIS POLYMERIZATION; RING-CLOSING METATHESIS; TRANSFER RADICAL-ADDITION; CARBOXYLIC-ACIDS; TERMINAL ALKYNES; RU COMPLEXES; VINYL ESTERS; IMIDAZOL(IN)IUM-2-CARBOXYLATES;
D O I
10.1016/j.jorganchem.2009.08.028
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The catalytic activity of four ruthenium imidazol(in)ium-2-dithiocarboxylates was evaluated for the synthesis of vinyl esters through addition of 4-acetoxybenzoic acid to 1-hexyne, and compared to those of the parent ruthenium-N-heterocyclic carbene complexes and [RuCl2(p-cymene)(PPh3)] (a standard catalyst). It turned out that ruthenium imidazol(in)ium-2-dithiocarboxylates were poorly active and selective. Quantitative yields, indeed, were obtained only after extended reaction times. However, the catalytic activity could be improved significantly under microwave heating or conventional heating in a sealed tube at 160 degrees C, driving the reaction to completion in less than 4 h of reaction. (C) 2009 Elsevier B. V. All rights reserved.
引用
收藏
页码:4049 / 4055
页数:7
相关论文
共 64 条
[1]   Microwave-assisted synthesis of N-heterocyclic carbene precursors [J].
Aidouni, A ;
Demonceau, A ;
Delaude, L .
SYNLETT, 2006, (03) :493-495
[2]   Facile Microwave-Assisted Synthesis of Cyclic Amidinium Salts [J].
Aidouni, Adila ;
Bendahou, Soufiane ;
Demonceau, Albert ;
Delaude, Lionel .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2008, 10 (06) :886-892
[3]   Recent developments in microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions [J].
Appukkuttan, Prasad ;
Van der Eycken, Erik .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (07) :1133-1155
[4]   ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE [J].
BENNETT, MA ;
SMITH, AK .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02) :233-241
[5]   OCTAHEDRAL NICKEL(II) DITHIOCARBOXYLATES [J].
BORER, LL ;
KONG, J ;
SINN, E .
INORGANICA CHIMICA ACTA, 1986, 122 (02) :145-148
[6]   METAL-COMPLEXES OF 1,3-DIMETHYLIMIDAZOLIUM-2-DITHIOCARBOXYLATE [J].
BORER, LL ;
KONG, JV ;
KEIHL, PA ;
FORKEY, DM .
INORGANICA CHIMICA ACTA, 1987, 129 (02) :223-226
[7]   Microwave-enhanced ruthenium-catalysed atom transfer radical additions [J].
Borguet, Yannick ;
Richel, Aurore ;
Delfosse, Sbastien ;
Leclerc, Alain ;
Delaude, Lionel ;
Demonceau, Albert .
TETRAHEDRON LETTERS, 2007, 48 (36) :6334-6338
[8]   RUTHENIUM-CATALYZED ADDITIONS TO ALKYNES - SYNTHESIS OF ACTIVATED ESTERS AND THEIR USE IN ACYLATION REACTIONS [J].
BRUNEAU, C ;
NEVEUX, M ;
KABOUCHE, Z ;
RUPPIN, C ;
DIXNEUF, PH .
SYNLETT, 1991, (11) :755-763
[9]   Selective transformations of alkynes with ruthenium catalysts [J].
Bruneau, C ;
Dixneuf, PH .
CHEMICAL COMMUNICATIONS, 1997, (06) :507-512
[10]   Microwave enhanced synthesis [J].
Caddick, Stephen ;
Fitzmaurice, Richard .
TETRAHEDRON, 2009, 65 (17) :3325-3355