Zirconocene bis(perfluorooctanesulfonate)s-catalyzed acylation of alcohols, phenols, thiols, and amines under solvent-free conditions

被引：37

作者：

Qiu, Renhua ^{[1
]}

Zhu, Yuyang ^{[1
]}

Xu, Xinhua ^{[1
]}

Li, Yinhui ^{[1
]}

Shao, Lingling ^{[1
]}

Ren, Xiaofang ^{[1
]}

Cai, Xitian ^{[1
]}

An, Delie ^{[1
]}

Yin, Shuangfeng ^{[1
]}

机构：

[1] Hunan Univ, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China

来源：

CATALYSIS COMMUNICATIONS | 2009年 / 10卷 / 14期

关键词：

Zirconocene; Perfluorooctanesulfonate; Lewis acid; Acyfation; Catalyst; LEWIS-ACID CATALYSTS; HOMOGENEOUS CATALYSIS; MIXED ANHYDRIDES; ACETIC-ANHYDRIDE; TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE; SCANDIUM TRIFLUOROMETHANESULFONATE; HIGHLY EFFICIENT; ESTERIFICATION; COMPLEX; BI(OTF)(3);

D O I：

10.1016/j.catcom.2009.06.019

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Air-stable zirconocene bis(perfluorooctanesulfonate)s [CP2Zr(OPf)(2), OPf = OSO2CsF17] showing high Lewis acidity and high thermal stability was prepared by reacting Cp2ZrCl2 with AgOPf, and examined as a catalyst for acylation reactions. It was found that in the acetylation of various alcohols, phenols, thiols, and amines by equimolar of acetic anhydride, Cp2Zr(OPf)(2) exhibits high activity and selectivity to desired products under mild and solvent-free conditions. In the acylation of 2-phenylethanol across various acylating reagents, it also shows good catalytic efficiency. In a test of ten cycles, Cp2Zr(OPf)(2) shows little loss of activity. The results afford a general and efficient method for the acylation of alcohols, phenols, thiols, and amines using zirconium bis(perfluorooctanesulfonate) as catalyst. (c) 2009 Elsevier B.V. All rights reserved.

引用

页码：1889 / 1892

页数：4

共 33 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] Facile catalyzed acylation of alcohols, phenols, amines and thiols based on ZrOCl28H2O and acetyl chloride in solution and in solvent-free conditions [J].

Ghosh, R ;

Maiti, S ;

Chakraborty, AJ .

TETRAHEDRON LETTERS, 2005, 46 (01) :147-151

[3] Scandium(III) perfluorooctanesulfonate [Sc(OPf)(3)]: A novel catalyst for the hetero Diels-Alder reaction of aldehydes with non-activated dienes [J].

Hanamoto, T ;

Sugimoto, Y ;

Jin, TZ ;

Inanaga, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (06) :1421-1426

[4] Metal bis(perfluorooctanesulfonyl)amides as highly efficient Lewis acid catalysts for fluorous biphase organic reactions [J].

Hao, XH ;

Yoshida, A ;

Nishikido, J .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (02) :193-199

[5] Recyclable and selective Lewis acid catalysts for transesterification and direct esterification in a fluorous biphase system: tin(IV) and hafnium(IV) bis(perfluorooctanesulfonyl)amide complexes [J].

Hao, XH ;

Yoshida, A ;

Nishikido, J .

TETRAHEDRON LETTERS, 2004, 45 (04) :781-785

[6] HOMOGENEOUS CATALYSIS - [TICP2(CF3SO3)2] AND [ZRCP2(CF3SO3)2THF], FAST AND EFFICIENT CATALYSTS FOR THE MUKAIYAMA CROSS-ALDOL REACTION [J].

HOLLIS, TK ;

ROBINSON, NP ;

BOSNICH, B .

TETRAHEDRON LETTERS, 1992, 33 (43) :6423-6426

[7] HOMOGENEOUS CATALYSIS - MECHANISMS OF THE CATALYTIC MUKAIYAMA ALDOL AND SAKURAI ALLYLATION REACTIONS [J].

HOLLIS, TK ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) :4570-4581

[8] HOMOGENEOUS CATALYSIS - [TI(CP-ASTERISK)2(H2O)2]2+ - AN AIR-STABLE, WATER-TOLERANT DIELS-ALDER CATALYST [J].

HOLLIS, TK ;

ROBINSON, NP ;

BOSNICH, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5464-5466

[9] 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

[10]

Ishihara K, 1996, SYNLETT, P265

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