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
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.
引用
收藏
页码:5902 / 5905
页数:4
相关论文
共 57 条
[51]   Sulfoximines: A Reusable Directing Group for Chemo- and Regioselective ortho C-H Oxidation of Arenes [J].
Yadav, M. Ramu ;
Rit, Raja K. ;
Sahoo, Akhila K. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (18) :5541-5545
[52]   Efficient palladium-catalyzed N-arylation of a sulfoximine with aryl chlorides [J].
Yongpruksa, Nattawut ;
Calkins, Nathan L. ;
Harmata, Michael .
CHEMICAL COMMUNICATIONS, 2011, 47 (27) :7665-7667
[53]   Metal-free cascade construction of C-C bonds by activation of inert C(sp3)-H bonds [J].
Zhang, Honglin ;
Pan, Changduo ;
Jin, Ning ;
Gu, Zhangxi ;
Hu, Hongwen ;
Zhu, Chengjian .
CHEMICAL COMMUNICATIONS, 2015, 51 (07) :1320-1322
[54]   Metal-free oxidative C(sp3)-H bond functionalization of alkanes and alkylation-initiated radical 1,2-aryl migration in α,α-diaryl allylic alcohols [J].
Zhao, Jincan ;
Fang, Hong ;
Song, Ruichun ;
Zhou, Jie ;
Han, Jianlin ;
Pan, Yi .
CHEMICAL COMMUNICATIONS, 2015, 51 (03) :599-602
[55]   Metal-Free Oxidative C(sp3)-H Bond Functionalization of Alkanes and Conjugate Addition to Chromones [J].
Zhao, Jincan ;
Fang, Hong ;
Qian, Ping ;
Han, Jianlin ;
Pan, Yi .
ORGANIC LETTERS, 2014, 16 (20) :5342-5345
[56]   Iron-Catalyzed Cross-Dehydrogenative Coupling Esterification of Unactive C(sp3)-H Bonds with Carboxylic Acids for the Synthesis of α-Acyloxy Ethers [J].
Zhao, Jincan ;
Fang, Hong ;
Zhou, Wei ;
Han, Jianlin ;
Pan, Yi .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (09) :3847-3855
[57]   Copper catalyzed direct alkenylation of simple alkanes with styrenes [J].
Zhu, Yefeng ;
Wei, Yunyang .
CHEMICAL SCIENCE, 2014, 5 (06) :2379-2382