Manganese-Catalyzed C-H Amidation of Heteroarenes in Water

被引:23
作者
Kong, Xianqiang [1 ]
Lin, Long [1 ]
Xu, Bo [1 ]
机构
[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Lu, Shanghai 201620, Peoples R China
基金
美国国家科学基金会;
关键词
C-H activations; manganese; directing group; amidation; TRACELESS DIRECTING GROUP; N; N-DIALKYL BENZAMIDES; ACTIVATION; FUNCTIONALIZATION; ARYLATION; IRIDIUM; HYDROARYLATION; ALKENES; ESTERS; SELECTIVITY;
D O I
10.1002/adsc.201800544
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We have developed an efficient manganese-catalyzed amidation of various heteroarenes via C-H bond activation using readily available sulfonyl azides. The key step is heteroarene directed electrophilic aromatic metalation using MnBr(CO)(5) as catalyst. This method offers excellent chemical yields and regioselectivity with good functional group tolerance. This base metal catalyzed reaction proceeds efficiently using water as the only solvent and nitrogen is the only byproduct.
引用
收藏
页码:2801 / 2805
页数:5
相关论文
共 50 条
[21]   Manganese-catalyzed bicyclic annulations of imines and α,β-unsaturated esters via C-H activation [J].
Hu, Yuanyuan ;
Wang, Congyang .
SCIENCE CHINA-CHEMISTRY, 2016, 59 (10) :1301-1305
[22]   Manganese-catalyzed bicyclic annulations of imines and α,β-unsaturated esters via C-H activation [J].
Yuanyuan Hu ;
Congyang Wang .
Science China(Chemistry), 2016, (10) :1301-1305
[23]   Manganese-Catalyzed Synthesis of cis-β-Amino Acid Esters through Organometallic C-H Activation of Ketimines [J].
Liu, Weiping ;
Zell, Daniel ;
John, Michael ;
Ackermann, Lutz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :4092-4096
[24]   Site- and Enantioselective Manganese-Catalyzed Benzylic C-H Azidation of Indolines [J].
Cao, Min ;
Wang, Hongliang ;
Ma, Yingang ;
Tung, Chen-Ho ;
Liu, Lei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (33) :15383-15390
[25]   Amine-accelerated manganese-catalyzed aromatic C-H conjugate addition to α,β-unsaturated carbonyls [J].
Zhou, Bingwei ;
Ma, Pengchen ;
Chen, Hui ;
Wang, Congyang .
CHEMICAL COMMUNICATIONS, 2014, 50 (93) :14558-14561
[26]   Chemodivergent manganese-catalyzed C-H activation: modular synthesis of fluorogenic probes [J].
Kaplaneris, Nikolaos ;
Son, Jongwoo ;
Mendive-Tapia, Lorena ;
Kopp, Adelina ;
Barth, Nicole D. ;
Maksso, Isaac ;
Vendrell, Marc ;
Ackermann, Lutz .
NATURE COMMUNICATIONS, 2021, 12 (01)
[27]   Manganese-catalyzed allylation via sequential C-H and C-C/C-Het bond activation [J].
Lu, Qingquan ;
Klauck, Felix J. R. ;
Glorius, Frank .
CHEMICAL SCIENCE, 2017, 8 (05) :3379-3383
[28]   Polycyclization Enabled by Relay Catalysis: One-Pot Manganese-Catalyzed C-H Allylation and Silver-Catalyzed Povarov Reaction [J].
Chen, Shi-Yong ;
Li, Qingjiang ;
Liu, Xu-Ge ;
Wu, Jia-Qiang ;
Zhang, Shang-Shi ;
Wang, Honggen .
CHEMSUSCHEM, 2017, 10 (11) :2360-2364
[29]   Indazolones Directed Rh(III)-Catalyzed C-H Amidation of Arenes [J].
Chen, Shao-Yong ;
Zheng, Yi-Chuan ;
Liu, Xu-Ge ;
Song, Jia-Lin ;
Shu, Bing ;
Zheng, Tao ;
Xiao, Lin ;
Zhang, Shang-Shi ;
Cao, Hua .
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) :3302-3309
[30]   Palladium(II)-Catalyzed Oxidative C-H/C-H Cross-Coupling of Heteroarenes [J].
Xi, Peihua ;
Yang, Fan ;
Qin, Song ;
Zhao, Dongbing ;
Lan, Jingbo ;
Gao, Ge ;
Hu, Changwei ;
You, Jingsong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1822-+