Transition-Metal-Free Intermolecular Amination of sp3 C-H Bonds with Sulfonamides

被引：125

作者：

Fan, Renhua ^{[1
]}

Li, Weixun ^{[1
]}

Pu, Dongming ^{[1
]}

Zhang, Li ^{[1
]}

机构：

[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 06期

基金：

中国国家自然科学基金;

关键词：

ACTIVATED METHYLENE-COMPOUNDS; VINYLIC HALOGEN SUBSTITUTION; POLYVALENT IODINE COMPOUNDS; COPPER-CATALYZED AMIDATION; RADICAL CYCLIZATION; ORGANOHYPERVALENT IODINE; INDUCED AZIRIDINATION; RUTHENIUM PORPHYRINS; AMIDYL RADICALS; MILD CONDITIONS;

D O I：

10.1021/ol900090f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient transition-metal-free intermolecular benzylic amidation with sulfonamides is described. Various valuable nitrogen-containing compounds, including amines, beta-chloro amine, amino alcohol, alpha-, beta-amino ester, and N-sulfonyl imine, are generated from the preferential N-functionalization of saturated benzylic C-H bonds. The potential of this reaction system also lies in the fact it can be developed into an environmentally friendly intermolecular amidation process.

引用

页码：1425 / 1428

页数：4

共 69 条

[31]

Koser GF, 2003, TOP CURR CHEM, V224, P137

[32] COPPER-CATALYZED DECOMPOSITION OF BENZENESULFONYL AZIDE IN CYCLOHEXENE SOLUTION [J].

KWART, H ;

KHAN, AA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (08) :1951-&

[33] N-tosyloxycarbamates as a source of metal nitrenes:: Rhodium-catalyzed C-H insertion and aziridination reactions [J].

Lebel, H ;

Huard, K ;

Lectard, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (41) :14198-14199

[34] Imido transfer from bis(imido)ruthenium(VI) porphyrins to hydrocarbons: Effect of imido substituents, C-H bond dissociation energies, and RUVIN reduction potentials [J].

Leung, SKY ;

Tsui, WM ;

Huang, JS ;

Che, CM ;

Liang, JL ;

Zhu, NY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (47) :16629-16640

[35] Silver-catalyzed intermolecular amination of C-H groups [J].

Li, Zigang ;

Capretto, D. A. ;

Rahaman, R. ;

He, Chuan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (27) :5184-5186

[36] Toward a synthetically useful stereoselective C-H amination of hydrocarbons [J].

Liang, Chungen ;

Collet, Florence ;

Robert-Peillard, Fabien ;

Mueller, Paul ;

Dodd, Robert H. ;

Dauban, Philippe .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (01) :343-350

[37] Intramolecular C-N bond formation reactions catalyzed by ruthenium porphyrins: Amidation of sulfamate esters and aziridination of unsaturated sulfonamides [J].

Liang, JL ;

Yuan, SX ;

Huang, JS ;

Che, CM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11) :3610-3619

[38]

Liang JL, 2002, ANGEW CHEM INT EDIT, V41, P3465, DOI 10.1002/1521-3773(20020916)41:18<3465::AID-ANIE3465>3.0.CO

[39]

2-D

[40] 5-exo versus 6-endo cyclization of primary aminyl radicals:: An experimental and theoretical investigation [J].

Liu, Feng ;

Liu, Kun ;

Yuan, Xinting ;

Li, Chaozhong .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :10231-10234

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