O-BENZENEDISULFONIMIDE AS A REUSABLE BRONSTED ACID CATALYST FOR HETERO-MICHAEL REACTIONS

被引：17

作者：

Barbero, Margherita ^{[1
]}

Cadamuro, Silvano ^{[1
]}

Dughera, Stefano ^{[1
]}

机构：

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

来源：

SYNTHETIC COMMUNICATIONS | 2013年 / 43卷 / 05期

关键词：

Bronsted acid; conjugate addition; homogeneous catalysis; Michael reaction; recyclable catalyst; ALPHA; BETA-UNSATURATED CARBONYL-COMPOUNDS; BETA-AMINO ACIDS; SOLVENT-FREE; ADDITION-REACTIONS; IONIC LIQUID; CONJUGATE ADDITION; SILICA-GEL; NUCLEOPHILES; NITROGEN; SULFUR;

D O I：

10.1080/00397911.2011.614834

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and alpha,beta-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Bronsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages.

引用

页码：758 / 767

页数：10

共 34 条

[1] Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3 [J].

Alam, MM ;

Varala, R ;

Adapa, SR .

TETRAHEDRON LETTERS, 2003, 44 (27) :5115-5119

[2] OXIDATIVE FUNCTIONALIZATION OF THE BETA-CARBON IN ALPHA,BETA-UNSATURATED SYSTEMS - PREPARATION OF 3-PHENYLTHIO ENONES, ACRYLATES, AND OTHER VINYL DERIVATIVES [J].

BAKUZIS, P ;

BAKUZIS, MLF .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (02) :235-239

[3] Synthesis of anticancer β-lactams:: mechanism of action [J].

Banik, BK ;

Becker, FF ;

Banik, I .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (10) :2523-2528

[4] o-Benzenedisulfonimide: An Organic Reagent and Organocatalyst of Renewed Interest [J].

Barbero, M. ;

Bazzi, S. ;

Cadamuro, S. ;

Dughera, S. .

CURRENT ORGANIC CHEMISTRY, 2011, 15 (04) :576-599

[5] 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

[6] o-Benzenedisulfonimide and its chiral derivative as Bronsted acids catalysts for one-pot three-component Strecker reaction. Synthetic and mechanistic aspects [J].

Barbero, Margherita ;

Cadamuro, Silvano ;

Dughera, Stefano ;

Ghigo, Giovanni .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (20) :4058-4068

[7]

Cardillo C., 1996, CHEM SOC REV, V25, P117

[8] CARBONYL-PROTECTED BETA-LITHIO ALDEHYDES AND KETONES VIA REDUCTIVE LITHIATION - A GENERAL PREPARATIVE METHOD FOR REMARKABLY VERSATILE HOMOENOLATE EQUIVALENTS [J].

CHERKAUSKAS, JP ;

COHEN, T .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :6-8

[9] Solvent-Promoted and -Controlled Aza-Michael Reaction with Aromatic Amines [J].

De, Kavita ;

Legros, Julien ;

Crousse, Benoit ;

Bonnet-Delpon, Daniele .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (16) :6260-6265

[10] TUMOR INHIBITORS HAVING POTENTIAL FOR INTERACTION WITH MERCAPTO ENZYMES AND-OR COENZYMES - REVIEW [J].

FUJITA, E ;

NAGAO, Y .

BIOORGANIC CHEMISTRY, 1977, 6 (03) :287-309

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