Efficient and selective nitrile hydration reactions in water catalyzed by an unexpected dimethylsulfinyl anion generated in situ from CsOH and DMSO

被引：61

作者：

Chen, Haonan ^{[1
]}

Dai, Wujie ^{[1
]}

Chen, Yi ^{[1
]}

Xu, Qing ^{[1
]}

Chen, Jianhui ^{[1
]}

Yu, Lei ^{[1
,2
]}

Zhao, Yajuan ^{[1
]}

Ye, Mingde ^{[1
]}

Pan, Yuanjiang ^{[1
,3
]}

机构：

[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Zhejiang, Peoples R China

[2] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China

[3] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

GREEN CHEMISTRY | 2014年 / 16卷 / 04期

关键词：

BASIC HYDROGEN-PEROXIDE; ARYL HALIDES; ALKOXYSULFONIUM IONS; FACILE SYNTHESIS; N-ALKYLATION; AMIDES; MECHANISM; ALCOHOLS; SULFOXIDE; OXIDATION;

D O I：

10.1039/c3gc42310g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Unexpected dimethylsulfinyl anions (I), generated in situ from the superbase system CsOH-DMSO, was found to be a highly active catalyst for controllable nitrile hydration reactions in water, which selectively afforded the versatile amides via interesting Cs-activated I-catalyzed direct and indirect hydration mechanisms involving an O-transfer process from DMSO onto the nitriles.

引用

页码：2136 / 2141

页数：6

共 73 条

[1] Frontiers in catalytic nitrile hydration: Nitrile and cyanohydrin hydration catalyzed by homogeneous organometallic complexes [J].

Ahmed, Takiya J. ;

Knapp, Spring Melody M. ;

Tyler, David R. .

COORDINATION CHEMISTRY REVIEWS, 2011, 255 (7-8) :949-974

[2] Metal-catalysed approaches to amide bond formation [J].

Allen, C. Liana ;

Williams, Jonathan M. J. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415

[3] Oxidative Hydroxylation Mediated by Alkoxysulfonium Ions [J].

Ashikari, Yosuke ;

Nokami, Toshiki ;

Yoshida, Jun-ichi .

ORGANIC LETTERS, 2012, 14 (03) :938-941

[4] Integrated Electrochemical-Chemical Oxidation Mediated by Alkoxysulfonium Ions [J].

Ashikari, Yosuke ;

Nokami, Toshiki ;

Yoshida, Jun-ichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (31) :11840-11843

[5] Potassium Hydroxide/Dimethyl Sulfoxide Promoted Intramolecular Cyclization for the Synthesis of Benzimidazol-2-ones [J].

Beyer, Astrid ;

Reucher, Christine M. M. ;

Bolm, Carsten .

ORGANIC LETTERS, 2011, 13 (11) :2876-2879

[6] Methylsulfinyl (Dimsyl) Anion as Umpolung Catalyst for the Chemoselective Cross-Benzoin Reaction of α-Diketones with Aldehydes [J].

Bortolini, Olga ;

Fantin, Giancarlo ;

Ferretti, Valeria ;

Fogagnolo, Marco ;

Giovannini, Pier Paolo ;

Massi, Alessandro ;

Pacifico, Salvatore ;

Ragno, Daniele .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (16) :3244-3252

[7] METAL-CATALYZED HYDRATION OF PHENANTHROLINE NITRILE [J].

BRESLOW, R ;

FAIRWEAT.R ;

KEANA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (09) :2135-&

[8] DEUTEROXIDE-CATALYZED HYDROGEN EXCHANGE OF DIMETHYL SULPHOXIDE . PREPARATION OF DIPERDEUTEROMETHYL SULPHOXIDE (CD3)2SO [J].

BUNCEL, E ;

SYMONS, EA ;

ZABEL, AW .

CHEMICAL COMMUNICATIONS, 1965, (09) :173-&

[9] Concerning the denticity of the dimethylsulfinyl anion in Meisenheimer complexation [J].

Buncel, E ;

Park, KT ;

Dust, JM ;

Manderville, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (18) :5388-5392

[10]

CACCHI S, 1980, SYNTHESIS-STUTTGART, P243

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