Synthesis of Sulfonated Oxindoles by Potassium Iodide Catalyzed Arylsulfonylation of Activated Alkenes with Sulfonylhydrazides in Water

被引：226

作者：

Li, Xiaoqing ^{[1
]}

Xu, Xiangsheng ^{[1
]}

Hu, Peizhu ^{[1
]}

Xiao, Xuqiong ^{[2
]}

Zhou, Can ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310014, Zhejiang, Peoples R China

[2] Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 310012, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 14期

基金：

中国国家自然科学基金;

关键词：

H BOND ACTIVATION; OXIDATIVE ARYLALKYLATION; ALLYLIC SULFONYLATION; ROOM-TEMPERATURE; FUNCTIONALIZATION; ACETONITRILE; ALDEHYDES; CLEAVAGE; OXIDANT; AMIDES;

D O I：

10.1021/jo401069d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic system consisting of KI, 18-crown-6, and TBHP for arylsulfonylation of activated alkenes with sulfonylhydrazides as sulfonyl precursor is described. This protocol provides a practical and environmentally benign method for the construction of sulfonated oxindoles in water.

引用

页码：7343 / 7348

页数：6

共 31 条

[1]

Bertrand M. P., 2001, RADICALS ORGANIC SYN, V2, P485

[2] One-Pot Synthesis of Amides from Aldehydes and Amines via C-H Bond Activation [J].

Cadoni, Roberta ;

Porcheddu, Andrea ;

Giacomelli, Giampaolo ;

De Luca, Lidia .

ORGANIC LETTERS, 2012, 14 (19) :5014-5017

[3] Catalytic Asymmetric Mannich Reactions of Sulfonylacetates [J].

Cassani, Carlo ;

Bernardi, Luca ;

Fini, Francesco ;

Ricci, Alfredo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (31) :5694-5697

[4] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[5] Metal-Free Synthesis of 3,3-Disubstituted Oxoindoles by Iodine(III)-Catalyzed Bromocarbocyclizations [J].

Fabry, David C. ;

Stodulski, Maciej ;

Hoerner, Stefanie ;

Gulder, Tanja .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (35) :10834-10838

[6] Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C-H functionalization [J].

Hennessy, EJ ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (40) :12084-12085

[7] Oxindole Synthesis by Direct Coupling of Csp2-H and Csp3-H Centers [J].

Jia, Yi-Xia ;

Kuendig, E. Peter .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (09) :1636-1639

[8] Copper-catalyzed C-N bond formation through C-H/N-H activation: a novel approach to the synthesis of multisubstituted ureas [J].

Jiang, Honglai ;

Lin, Aijun ;

Zhu, Chengjian ;

Cheng, Yixiang .

CHEMICAL COMMUNICATIONS, 2013, 49 (08) :819-821

[9] Isotope effects in C-H bond activation reactions by transition metals [J].

Jones, WD .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (02) :140-146

[10] ISOTOPE EFFECTS IN ARENE C-H BOND ACTIVATION BY [(C5ME5)RH(PME3)] [J].

JONES, WD ;

FEHER, FJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (16) :4814-4819

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