Copper-catalyzed oxidative C(sp3)-H/N-H coupling of sulfoximines and amides with simple alkanes via a radical process

被引：90

作者：

Teng, Fan ^{[1
]}

Sun, Song ^{[1
]}

Jiang, Yan ^{[1
]}

Yu, Jin-Tao ^{[1
]}

Cheng, Jiang ^{[1
]}

机构：

[1] Changzhou Univ, Jiangsu Prov Key Lab Fine Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Sch Petrochem Engn, Changzhou 213164, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 27期

基金：

中国国家自然科学基金;

关键词：

H BOND ACTIVATION; BENZOTHIAZINE LIGAND; ALLYLIC ESTERS; ARYL IODIDES; N-ARYLATION; ARENES; NITROGEN; ACIDS; FUNCTIONALIZATION; ALKENES;

D O I：

10.1039/c5cc00839e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A copper-catalyzed oxidative C(sp(3))-H/N-H coupling of sulfoximines with simple alkanes was developed. This protocol involved C(sp(3))-N bond formation via a radical pathway and tolerated a series of functional groups, such as chloro, methyl and aryl, on the phenyl rings. Apart from sulfoximines, amides, saccharin and aniline also worked well to give the corresponding N-alkylated products.

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收藏

页码：5902 / 5905

页数：4

相关论文

共 57 条

[21] N-(TRIMETHYLSILYL)METHYLPHENYLSULFOXIMINE - A CONVENIENT INTERMEDIATE FOR THE PREPARATION OF FUNCTIONALIZED SULFOXIMINES [J].

HWANG, KJ .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (01) :99-101

[22] ALKYLATION OF SULFOXIMINES AND RELATED-COMPOUNDS AT THE IMINO NITROGEN UNDER PHASE-TRANSFER CONDITIONS [J].

JOHNSON, CR ;

LAVERGNE, OM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07) :1922-1923

[23] UTILIZATION OF SULFOXIMINES AND DERIVATIVES AS REAGENTS FOR ORGANIC SYNTHESIS [J].

JOHNSON, CR .

ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (10) :341-347

[24]

Komiya N., 2001, CHEM COMMUN, V65

[25] A Free Radical Cascade Cyclization of Isocyanides with Simple Alkanes and Alcohols [J].

Li, Zejiang ;

Fan, Fenghua ;

Yang, Jie ;

Liu, Zhong-Quan .

ORGANIC LETTERS, 2014, 16 (12) :3396-3399

[26] Free-Radical Cascade Alkylarylation of Alkenes with Simple Alkanes: Highly Efficient Access to Oxindoles via Selective (sp3)C-H and (sp2)C-H Bond Functionalization [J].

Li, Zejiang ;

Zhang, Ye ;

Zhang, Lizhi ;

Liu, Zhong-Quan .

ORGANIC LETTERS, 2014, 16 (02) :382-385

[27] Recent Advances of Transition-Metal Catalyzed Radical Oxidative Cross-Couplings [J].

Liu, Chao ;

Liu, Dong ;

Lei, Aiwen .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (12) :3459-3470

[28] Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O2 [J].

Liu, Jie ;

Liu, Qiang ;

Yi, Hong ;

Qin, Chu ;

Bai, Ruopeng ;

Qi, Xiaotian ;

Lan, Yu ;

Lei, Aiwen .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :502-506

[29] Oxidative Catalytic Coupling Reactions: Selective Formation of C-C and C-X Bonds Using Radical Processes [J].

Liu, Qiang ;

Jackstell, Ralf ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (52) :13871-13873

[30] Manganese Porphyrins Catalyze Selective C-H Bond Halogenations [J].

Liu, Wei ;

Groves, John T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) :12847-12849

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