A mild and efficient acetylation of alcohols, phenols and amines with acetic anhydride using La(NO3)3•6H2O as a catalyst under solvent-free conditions

被引:90
作者
Reddy, T. Srikanth [1 ]
Narasimhulu, M. [1 ]
Suryakiran, N. [1 ]
Mahesh, K. Chinni [1 ]
Ashalatha, K. [1 ]
Venkateswarlu, Y. [1 ]
机构
[1] Indian Inst Chem Technol, Nat Prod Lab, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India
关键词
lanthanum(III) nitrate hexahydrate; alcohols; phenols; amines; acetylation; solvent-free conditions;
D O I
10.1016/j.tetlet.2006.07.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A wide variety of alcohols, phenols and amines are efficiently and selectively converted into the corresponding acetates by treatment with acetic anhydride in the presence of catalytic amounts of La(NO3)(3)center dot 6H(2)O under solvent-free conditions at room temperature. The method is compatible with acid sensitive hydroxyl protecting groups such as TBDMS, THP, OBz, OBn, Boc and some isopropylidenes and offers excellent yields of the mono acetates of 1,3-, 1,4- and 1,5-diols. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6825 / 6829
页数:5
相关论文
共 23 条
[1]   Scandium(III) or lanthanide(III) triflates as recyclable catalysts for the direct acetylation of alcohols with acetic acid [J].
Barrett, AGM ;
Braddock, DC .
CHEMICAL COMMUNICATIONS, 1997, (04) :351-352
[2]   Per-O-acetylation of sugars catalysed by montmorillonite K-10 [J].
Bhaskar, PM ;
Loganathan, D .
TETRAHEDRON LETTERS, 1998, 39 (15) :2215-2218
[3]   Acylation of alcohols with acetic anhydride catalyzed by TaCl5:: Some implications in kinetic resolution [J].
Chandrasekhar, S ;
Ramachander, T ;
Takhi, M .
TETRAHEDRON LETTERS, 1998, 39 (20) :3263-3266
[4]  
Chauhan KK, 1999, SYNLETT, P1743
[5]  
Greene T.W., 1991, PROTECTIVE GROUPS OR, V2nd
[6]   4-DIALKYLAMINOPYRIDINES AS ACYLATION CATALYSTS .4. 4-DIALKYLAMINOPYRIDINES AS HIGHLY ACTIVE ACYLATION CATALYSTS [J].
HOFLE, G ;
STEGLICH, W ;
VORBRUGGEN, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (08) :569-&
[7]   COBALT(II) CHLORIDE CATALYZED ACYLATION OF ALCOHOLS WITH ACETIC-ANHYDRIDE - SCOPE AND MECHANISM [J].
IQBAL, J ;
SRIVASTAVA, RR .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2001-2007
[8]  
Ishihara K, 1996, SYNLETT, P265
[9]   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
[10]   Scandium trifluoromethanesulfonate as an extremely active Lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides [J].
Ishihara, K ;
Kubota, M ;
Kurihara, H ;
Yamamoto, H .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4560-4567