Metal triflates-methanesulfonic acid as new catalytic systems: application to the Fries rearrangement

被引:32
作者
Mouhtady, O
Gaspard-Iloughmane, H
Roques, N
Le Roux, C
机构
[1] Univ Toulouse 3, UMR 5069, CNRS, F-31062 Toulouse 04, France
[2] Ctr Rech Lyon, Rhodia Organ Fine, F-69192 St Fons, France
关键词
D O I
10.1016/S0040-4039(03)01599-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A surprising synergistic effect has been discovered between metal triflates (Mg, Ca, Sc, Cu, Zn, Y, Ln, Bi) and methanesulfonic acid, leading to active catalytic systems for the Fries rearrangement. In particular, the systems based on yttrium and copper(II) triflate proved to be very active and much cheaper than scandium triflate. The efficiency of these systems might result from the catalytic Lewis acid activation of Bronsted acids. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6379 / 6382
页数:4
相关论文
共 31 条
[1]   Three component synthesis of homoallylic amines. Efficient catalysis by lanthanum triflate/benzoic acid [J].
Aspinall, HC ;
Bissett, JS ;
Greeves, N ;
Levin, D .
TETRAHEDRON LETTERS, 2002, 43 (02) :323-325
[2]   Lanthanum triflate-catalysed allylation of aldehydes: crucial activation by benzoic acid [J].
Aspinall, HC ;
Bissett, JS ;
Greeves, N ;
Levin, D .
TETRAHEDRON LETTERS, 2002, 43 (02) :319-321
[3]  
Bensari A, 2003, SYNTHESIS-STUTTGART, P267
[4]   A remarkable ene-like reaction: Development and synthetic applications [J].
Ciufolini, MA ;
Deaton, MV ;
Zhu, SR ;
Chen, MY .
TETRAHEDRON, 1997, 53 (48) :16299-16312
[5]   Fries rearrangement in methane sulfonic acid, an environmental friendly acid [J].
Commarieu, A ;
Hoelderich, W ;
Laffitte, JA ;
Dupont, MP .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 182 (01) :137-141
[6]   NEW ASPECTS OF FRIES REARRANGEMENT [J].
EFFENBERGER, F ;
KLENK, H ;
LUDWIG, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1973, 12 (09) :775-776
[7]   BORON-TRIS(TRIFLUOROMETHANE-SULFONATE), B(OSO2CF3)3, IN TRIFLUOROMETHANE SULFONIC-ACID - NEW SUPER ACID SYSTEM [J].
ENGELBRECHT, A ;
TSCHAGER, E .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1977, 433 (01) :19-25
[8]   On homologues of coumaranone and their derivatives. [J].
Fries, K ;
Finck, G .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1908, 41 :4271-4284
[9]  
GERECS A, 1964, FRIEDEL CRAFTS RELAT, V3, P499
[10]  
Hertweck C, 2000, J PRAK CHEM-CHEM ZTG, V342, P316, DOI 10.1002/(SICI)1521-3897(200003)342:3<316::AID-PRAC316>3.0.CO