Cationic Cobalt(III)-Catalyzed Aryl and Alkenyl CH Amidation: A Mild Protocol for the Modification of Purine Derivatives

被引：154

作者：

Liang, Yujie ^{[1
]}

Liang, Yu-Feng ^{[1
]}

Tang, Conghui ^{[1
]}

Yuan, Yizhi ^{[1
]}

Jiao, Ning ^{[1
,2
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

[2] Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 46期

基金：

美国国家科学基金会;

关键词：

amidation; CH functionalization; CN bond formation; cobalt; purine compounds; H BOND ACTIVATION; N-TYPE REACTIONS; 6-ARYLPURINE NUCLEOSIDES; CYTOSTATIC ACTIVITY; DIRECT ARYLATION; CATALYZED CH; ACYL AZIDES; FUNCTIONALIZATION; CLEAVAGE; PHOTOLYSIS;

D O I：

10.1002/chem.201503533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A cationic cobalt(III)-catalyzed direct CH amidation of unactivated (hetero)arenes and alkenes by using 1,4,2-dioxazol-5-ones as the amidating reagent has been developed. This transformation proceeds efficiently under external oxidant-free conditions with a broad substrate scope. Moreover, 6-arylpurine compounds, which often exhibit high potency in antimycobacterial, cytostatic, and anti-HCV activities, can be smoothly amidated, thus offering a mild protocol for their late stage functionalization.

引用

页码：16395 / 16399

页数：5

共 90 条

[21] Low-Valent Cobalt Catalysis: New Opportunities for C-H Functionalization [J].

Gao, Ke ;

Yoshikai, Naohiko .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (04) :1208-1219

[22] Cobalt-Catalyzed Ortho Alkylation of Aromatic Imines with Primary and Secondary Alkyl Halides [J].

Gao, Ke ;

Yoshikai, Naohiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (25) :9279-9282

[23] Regioselectivity-Switchable Hydroarylation of Styrenes [J].

Gao, Ke ;

Yoshikai, Naohiko .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (03) :400-402

[24] The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].

Girard, Simon A. ;

Knauber, Thomas ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100

[25]

Grigorjeva L., 2014, ANGEW CHEM, V126, P10373

[26] Cobalt-Catalyzed, Aminoquinoline-Directed C(sp2)-H Bond Alkenylation by Alkynes [J].

Grigorjeva, Liene ;

Daugulis, Olafs .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (38) :10209-10212

[27] Cobalt-Catalyzed, Aminoquinoline-Directed Coupling of sp2 C-H Bonds with Alkenes [J].

Grigorjeva, Liene ;

Daugulis, Olafs .

ORGANIC LETTERS, 2014, 16 (17) :4684-4687

[28] Synthesis and antimycobacterial activity of 6-arylpurines:: The requirements for the N-9 substituent in active antimycobacterial purines [J].

Gundersen, LL ;

Nissen-Meyer, J ;

Spilsberg, B .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (06) :1383-1386

[29] Palladium-catalyzed C-H bond functionalization of C6-arylpurines [J].

Guo, Hai-Ming ;

Rao, Wei-Hao ;

Niu, Hong-Ying ;

Jiang, Li-Li ;

Meng, Ge ;

Jin, Jia-Jia ;

Yang, Xi-Ning ;

Qu, Gui-Rong .

CHEMICAL COMMUNICATIONS, 2011, 47 (19) :5608-5610

[30] Pd(II)-Catalyzed Ortho Arylation of 6-Arylpurines with Aryl Iodides via Purine-Directed C-H Activation: A New Strategy for Modification of 6-Arylpurine Derivatives [J].

Guo, Hai-Ming ;

Jiang, Li-Li ;

Niu, Hong-Ying ;

Rao, Wei-Hao ;

Liang, Lei ;

Mao, Run-Ze ;

Li, De-Yang ;

Qu, Gui-Rong .

ORGANIC LETTERS, 2011, 13 (08) :2008-2011

← 1 2 3 4 5 6 7 8 9 →