Direct C-H Arylation of N-Heterocycles with Aryl Triazenes Using Molecular Oxygen as Oxidant

被引:13
作者
Chaubey, Narendra R. [1 ]
Vishwakarma, Ramesh Kumar [1 ]
Singh, Krishna Nand [1 ]
机构
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
来源
CHEMISTRYSELECT | 2019年 / 4卷 / 29期
关键词
Arylation; aryl triazene; metal-free; N-Heterocycles; peroxide-free; ELECTRON-DEFICIENT HETEROCYCLES; METAL-FREE; SULFONYL HYDRAZIDES; PRACTICAL SYNTHESIS; CATALYZED SYNTHESIS; BOND FORMATION; ISOQUINOLINES; HETEROARENES; ACIDS; (HETERO)ARENES;
D O I
10.1002/slct.201901144
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient C-H arylation of N-heterocycles has been developed using stable and easily accessible aryl triazenes in the presence of oxygen under metal- and peroxide-free conditions. The methodology is regiospecific and applicable to a wide range of electron-deficient N-heterocycles and aryl triazenes as demonstrated by 20 examples with yields ranging from 32-83%.
引用
收藏
页码:8522 / 8525
页数:4
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[21]   Anomalous substituent effects in the Bischler-Napieralski reaction of 2-aryl aromatic formamides [J].
Ishikawa, T ;
Shimooka, K ;
Narioka, T ;
Noguchi, S ;
Saito, T ;
Ishikawa, A ;
Yamazaki, E ;
Harayama, T ;
Seki, H ;
Yamaguchi, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9143-9151
[22]  
j stomo F. P. Cris, 2014, ANGEW CHEM, V126, P2213
[23]   Nickel Catalyzed Ipso-hydroxylation and Subsequent Cross Dehydrogenative Coupling of Arylboronic Acids with Tertiary Amines: A Facile Access to α-phenolated Tertiary Amines [J].
Kumar, Promod ;
Sharma, Anup Kumar ;
Singh, Rahul ;
Guntreddi, Tirumaleswararao ;
Singh, Krishna Nand .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (09) :1786-1789
[24]   Transition-Metal-Free Regiospecific Aroylation of Nitroarenes Using Ethyl Arylacetates at Room Temperature [J].
Kumar, Promod ;
Sharma, Anup Kumar ;
Guntreddi, Tirumaleswararao ;
Singh, Rahul ;
Singh, Krishna Nand .
ORGANIC LETTERS, 2018, 20 (03) :744-747
[25]   A practical protocol for the synthesis of bibenzyls via C(sp3)-H activation of methyl arenes under metal-free conditions [J].
Kumar, Promod ;
Guntreddi, Tirumaleswararao ;
Singh, Rahul ;
Singh, Krishna Nand .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01) :147-150
[26]  
Kumar S., 2018, EUR J ORG CHEM, V43, P59
[27]   Palladium Catalyzed C-C and C-N Bond Formation via ortho C-H Activation and Decarboxylative Strategy: A Practical Approach towards N-Acylated Indoles [J].
Kumar, Saurabh ;
Singh, Rahul ;
Singh, Krishna Nand .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (03) :422-426
[28]   A MODIFIED BISCHLER-NAPIERALSKI PROCEDURE FOR THE SYNTHESIS OF 3-ARYL-3,4-DIHYDROISOQUINOLINES [J].
LARSEN, RD ;
REAMER, RA ;
CORLEY, EG ;
DAVIS, P ;
GRABOWSKI, EJJ ;
REIDER, PJ ;
SHINKAI, I .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6034-6038
[29]   A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination [J].
Pandey, Anand Kumar ;
Kumar, Saurabh ;
Singh, Rahul ;
Singh, Krishna Nand .
TETRAHEDRON, 2018, 74 (46) :6704-6709
[30]   Suzuki cross-coupling/reductive debenzyloxycarbonylation sequence for the syntheses of [c]annulated isoquinolines:: Application for the syntheses of pancratistatin-like isoquinolines [J].
Pandey, Ganesh ;
Balakrishnan, Madhesan .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) :8128-8131