o-Benzenedisulfonimide as a Reusable Bronsted Acid Catalyst for Ritter-Type Reactions

被引：63

作者：

Barbero, Margherita ^{[1
]}

Bazzi, Stefano ^{[1
]}

Cadamuro, Silvano ^{[1
]}

Dughera, Stefano ^{[1
]}

机构：

[1] Univ Turin, Dipartimento Chim Gen & Chim Organ, I-10125 Turin, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 03期

关键词：

Homogeneous catalysis; Amides; Nitriles; Ritter reaction; Bronsted acid; SELECTIVE AMIDATION; EFFICIENT CATALYST; BENZYLIC ALCOHOLS; NITRILES; CONVERSION; AMIDES; SALTS;

D O I：

10.1002/ejoc.200800931

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions between various benzyl alcohols or tert-butyl alcohol and nitriles were carried out in the presence of catalytic amounts (usually 10-20 mol-%) of o-benzenedisulfonimide as a Bronsted acid catalyst; the reaction conditions were mild and the yields of amides were good. The catalyst was easily recovered and purified, ready to be used in further reactions, with economic and ecological advantages. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：430 / 436

页数：7

共 36 条

[1]

Barbero M, 1998, SYNTHESIS-STUTTGART, P1171

[2] o-benzenedisulfonimide as reusable Bronsted acid catalyst for acid-catalyzed organic reactions [J].

Barbero, Margherita ;

Cadamuro, Silvano ;

Dughera, Stefano ;

Venturello, Paolo .

SYNTHESIS-STUTTGART, 2008, (09) :1379-1388

[3] o-benzenedisulfonimide:: A novel and reusable catalyst for acid-catalyzed organic reactions [J].

Barbero, Margherita ;

Cadamuro, Silvano ;

Dughera, Stefano ;

Venturello, Paolo .

SYNLETT, 2007, (14) :2209-2212

[4] o-Benzenedisulfonimide as a Soft, Efficient, and Recyclable Catalyst for the Acylation of Alcohols, Phenols, and Thiols under Solvent-Free Conditions: Advantages and Limitations [J].

Barbero, Margherita ;

Cadamuro, Silvano ;

Dughera, Stefano ;

Venturello, Paolo .

SYNTHESIS-STUTTGART, 2008, 22 (22) :3625-3632

[5] CONVERSION OF ALCOHOLS INTO AMIDES USING CHLORODIPHENYLMETHYLIUM HEXACHLOROANTIMONATE IN NITRILE SOLVENTS [J].

BARTON, DHR ;

MAGNUS, PD ;

YOUNG, RN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (10) :331-332

[6]

Bishop R., 1991, Comp. Org. Synth, V6, P261

[7] POLYSULFONYL AMINES .40. PREPARATION OF SILVER(I) DISULFONYLAMIDE ACETONITRILE COMPLEXES - CHARACTERIZATION OF TETRAACETONITRILESILVER(I) BIS(DIMESYLAMIDO)ARGENTATE(I) AND (1,1,3,3-TETRAOXO-1,3,2-BENZODITHIAZOLIDO)ACETONITRILESILVER(I) BY X-RAY-DIFFRACTOMETRY AND THERMAL-ANALYSIS [J].

BLASCHETTE, A ;

JONES, PG ;

HAMANN, T ;

NAVEKE, M ;

SCHOMBURG, D ;

CAMMENGA, HK ;

EPPLE, M ;

STEPPUHN, I .

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1993, 619 (05) :912-922

[8] Synthesis of amides using the Ritter reaction with bismuth triflate catalysis [J].

Callens, Emmanuel ;

Burton, Andrew J. ;

Barrett, Anthony G. M. .

TETRAHEDRON LETTERS, 2006, 47 (49) :8699-8701

[9] Reaction of α,β-unsaturated ketones with LiAlH4 under oxygen:: synthesis of 1,3-diols [J].

Csáky, AG ;

Máximo, N ;

Plumet, J ;

Rámila, A .

TETRAHEDRON LETTERS, 1999, 40 (35) :6485-6487

[10] Improved synthesis of o-benzenedisulfonimide [J].

Davis, FA ;

Sundarababu, G ;

Qi, HY .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1998, 30 (01) :107-109

← 1 2 3 4 →