Rhodium(III)-Catalyzed Azidation and Nitration of Arenes by C-H Activation

被引:175
作者
Xie, Fang [1 ]
Qi, Zisong [1 ]
Li, Xingwei [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
关键词
azidation; CH activation; hypervalent iodine; nitration; rhodium; N BOND FORMATION; ARYL AZIDES; STEREOSELECTIVE NITRATION; AMIDATION; C(SP(2))-H; AMINATION; CHEMISTRY; OLEFINS; RH; PALLADIUM;
D O I
10.1002/anie.201305902
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Getting a handle on it: In the chelation-assisted title reactions in the presence of a hypervalent iodine oxidant, sodium azide and sodium nitrite served as readily available nitrogen sources, and pyridine, pyrimidine, and pyrazole substituents were efficient directing groups (DGs; see scheme; Cp*=C 5Me5). The synthetic utility of the azidation products was demonstrated in subsequent functional-group transformations. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11862 / 11866
页数:5
相关论文
共 78 条
[21]  
Feuer H., 1990, In Nitro Compounds: Recent Advances in Synthesis and Chemistry
[22]   Tantalum alkyl and silyl complexes of the bulky (terphenyl)imido ligand [2,6-(2,4,6-Me3C6H2)2C6H3N=]2-([Ar*N=]2-).: Generation and reactivity of [(Ar*N=)(Ar*NH)Ta(H)(OSO2CF3)], which reversibly transfers hydride to an aromatic ring of the arylamide ligand [J].
Gavenonis, J ;
Tilley, TD .
ORGANOMETALLICS, 2002, 21 (25) :5549-5563
[23]   Rhodium-Catalyzed Directed C-H Cyanation of Arenes with N-Cyano-N-phenyl-p-toluenesulfonamide [J].
Gong, Tian-Jun ;
Xiao, Bin ;
Cheng, Wan-Min ;
Su, Wei ;
Xu, Jun ;
Liu, Zhao-Jing ;
Liu, Lei ;
Fu, Yao .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (29) :10630-10633
[24]   Rh[III]-Catalyzed C-H Amidation Using Aroyloxycarbamates To Give N-Boc Protected Arylamines [J].
Grohmann, Christoph ;
Wang, Honggen ;
Glorius, Frank .
ORGANIC LETTERS, 2013, 15 (12) :3014-3017
[25]   Rh[III]-Catalyzed Direct C-H Amination Using N-Chloroamines at Room Temperature [J].
Grohmann, Christoph ;
Wang, Honggen ;
Glorius, Frank .
ORGANIC LETTERS, 2012, 14 (02) :656-659
[26]  
Guisado-Barrios G., 2010, ANGEW CHEM, V122, P4869
[27]   Crystalline 1H-1,2,3-Triazol-5-ylidenes: New Stable Mesoionic Carbenes (MICs) [J].
Guisado-Barrios, Gregorio ;
Bouffard, Jean ;
Donnadieu, Bruno ;
Bertrand, Guy .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (28) :4759-4762
[28]   Practical Azidation of 1,3-Dicarbonyls [J].
Harschneck, Tobias ;
Hummel, Sara ;
Kirsch, Stefan F. ;
Klahn, Philipp .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (04) :1187-1193
[29]   AIDS-DRIVEN NUCLEOSIDE CHEMISTRY [J].
HURYN, DM ;
OKABE, M .
CHEMICAL REVIEWS, 1992, 92 (08) :1745-1768
[30]   Rhodium(III)-Catalyzed Intermolecular Direct Amination of Aromatic C-H Bonds with N-Chloroamines [J].
Ka-Ho Ng ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
ORGANIC LETTERS, 2012, 14 (01) :272-275