Air-stable titanocene bis(perfluorooctanesulfonate) as a new catalyst for acylation of alcohols, phenols, thiols, and amines under solvent-free condition

被引:26
作者
Qiu, Renhua [1 ]
Zhang, Guoping [1 ]
Ren, Xiaofang [1 ]
Xu, Xinhua [1 ]
Yang, Ronghua [1 ]
Luo, Shenglian [1 ]
Yin, Shuangfeng [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China
基金
中国国家自然科学基金;
关键词
Acylation; Titanocene; Perfluorooctanesulfonate; Lewis acid; Catalyst; HIGHLY EFFICIENT CATALYST; SCANDIUM TRIFLUOROMETHANESULFONATE; HOMOGENEOUS CATALYSIS; PRACTICAL ACYLATION; VERSATILE CATALYST; CARBOXYLIC-ACIDS; ACETIC-ANHYDRIDE; SILICA-GEL; ACETYLATION; CHLORIDE;
D O I
10.1016/j.jorganchem.2010.01.025
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Air-stable titanocene bis(perfluorooctanesulfonate) [Cp2Ti(OSO2C8F17)(2)] that shows high Lewis acidity was prepared from Cp2TiCl2 and AgOSO2C8F17. The compound was characterized by different techniques, and examined as a catalyst for acylation reactions. It was found that using equimolar acetic anhydride as acetylating agent and under solvent-free condition, Cp2Ti(OSO2C8F17)(2) exhibits high activity and selectivity in the acetylation of various alcohols, phenols, thiols, and amines. Also, good catalytic efficiency is observed in the acylation of 2-phenylethanol across various acylating reagents. The catalyst can be reused without loss of activity in a test of ten cycles. The Cp2Ti(OSO2C8F17)(2) catalyst affords a simple, efficient and general method for the acylation of alcohols, phenols, thiols, and amines. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:1182 / 1188
页数:7
相关论文
共 51 条
[1]   Organotin perfluorooctanesulfonates as air-stable Lewis acid catalysts: Synthesis, characterization, and catalysis [J].
An, DL ;
Peng, ZH ;
Orita, A ;
Kurita, A ;
Man-e, S ;
Ohkubo, K ;
Li, XS ;
Fukuzumi, S ;
Otera, J .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (06) :1642-1647
[2]  
[Anonymous], 1999, PROTECTING GROUPS OR
[3]   Per-O-acetylation of sugars catalyzed by Ce(OTf)3 [J].
Bartoli, G ;
Dalpozzo, R ;
De Nino, A ;
Maiuolo, L ;
Nardi, M ;
Procopio, A ;
Tagarelli, A .
GREEN CHEMISTRY, 2004, 6 (04) :191-192
[4]   Zn(ClO4)2•6H2O as a powerful catalyst for a practical acylation of alcohols with acid anhydrides [J].
Bartoli, G ;
Bosco, M ;
Dalpozzo, R ;
Marcantoni, E ;
Massaccesi, M ;
Sambri, L .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (23) :4611-4617
[6]   ACIDITY OF CATALYST SURFACES .2. AMINE TITRATION USING HAMMETT INDICATORS [J].
BENESI, HA .
JOURNAL OF PHYSICAL CHEMISTRY, 1957, 61 (07) :970-973
[7]   Zirconium(IV) chloride as a new, highly efficient, and reusable catalyst for acetylation of phenols, thiols, amines, and alcohols under solvent-free conditions [J].
Chakraborti, AK ;
Gulhane, R .
SYNLETT, 2004, (04) :627-630
[8]  
Chakraborti AK, 2004, SYNTHESIS-STUTTGART, P111
[9]   Indium(III) chloride as a new, highly efficient, and versatile catalyst for acylation of phenols, thiols, alcohols, and amines [J].
Chakraborti, AK ;
Gulhane, R .
TETRAHEDRON LETTERS, 2003, 44 (35) :6749-6753
[10]   Fluoroboric acid adsorbed on silica gel as a new and efficient catalyst for acylation of phenols, thiols, alcohols, and amines [J].
Chakraborti, AK ;
Gulhane, R .
TETRAHEDRON LETTERS, 2003, 44 (17) :3521-3525