On the role of triflic acid in the metal triflate-catalysed acylation of alcohols

被引：96

作者：

Dumeunier, R ^{[1
]}

Markó, IE ^{[1
]}

机构：

[1] Univ Catholique Louvain, Unite Chim Organ & Medicinale, Dept Chim, B-1348 Louvain La Neuve, Belgium

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 04期

关键词：

triflic acid; acylation; metal triflate;

D O I：

10.1016/j.tetlet.2003.11.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The acylation of alcohols by anhydrides, catalysed by a wide range of metal triflates, is a powerful and mild method for the preparation of a variety of esters. Mechanistic insights demonstrate that triflic acid is generated under these reaction conditions and that, at least, two competing catalytic cycles are operating at the same time: a rapid one involving triflic acid and a slower one involving the metal triflate. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：825 / 829

页数：5

相关论文

共 31 条

[1] FACTORS AFFECTING THE INTERACTION OF LANTHANIDE SHIFT-REAGENTS WITH SUBSTITUTED PYRIDINES [J].

BALABAN, TS ;

UNCUTA, C ;

GHEORGHIU, MD ;

BALABAN, AT .

TETRAHEDRON LETTERS, 1985, 26 (38) :4669-4672

[2] PREPARATION AND REACTIONS OF 2,6-DI-T-BUTYLPYRIDINE AND RELATED HINDERED BASES . A CASE OF STERIC HINDRANCE TOWARD PROTON [J].

BROWN, HC ;

KANNER, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (05) :986-&

[3] 2,6-DI-BUTYLPYRIDINE - AN UNUSUAL PYRIDINE BASE [J].

BROWN, HC ;

KANNER, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3865-3865

[4] BENZOYL TRIFLUOROMETHANESULFONATE - A MILD REAGENT FOR THE BENZOYLATION OF STERICALLY HINDERED HYDROXYLS [J].

BROWN, L ;

KOREEDA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :3875-3880

[5]

Castellani CB, 1996, TETRAHEDRON, V52, P11045

[6]

Chauhan KK, 1999, SYNLETT, P1743

[7] CATALYTIC FRIEDEL-CRAFTS ACYLATION OF AROMATIC-COMPOUNDS [J].

EFFENBERGER, F ;

EPPLE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1972, 11 (04) :300-+

[8] Total synthesis and absolute configuration of polycavernoside A [J].

Fujiwara, K ;

Murai, A ;

Yotsu-Yamashita, M ;

Yasumoto, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (41) :10770-10771

[9]

Green W., 1999, PROTECTIVE GROUPS OR, P150

[10] SCANDIUM TRIFLUOROMETHANESULFONATE AS AN EXTREMELY ACTIVE ACYLATION CATALYST [J].

ISHIHARA, K ;

KUBOTA, M ;

KURIHARA, H ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (15) :4413-4414

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