Copper- or Nickel-Enabled Oxidative Cross-Coupling of Unreactive C(sp3)-H Bonds with Azole C(sp2)-H Bonds: Rapid Access to β-Azolyl Propanoic Acid Derivatives

被引：31

作者：

Tan, Guangying ^{[1
]}

Zhang, Luoqiang ^{[1
]}

Liao, Xingrong ^{[1
]}

Shi, Yang ^{[1
]}

Wu, Yimin ^{[1
]}

Yang, Yudong ^{[1
]}

You, Jingsong ^{[1
]}

机构：

[1] Sichuan Univ, Key Lab Green Chem & Technol, Minist Educ, Coll Chem, 29 Wangjiang Rd, Chengdu 610064, Sichuan, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 18期

关键词：

DEHYDROGENATIVE HETEROARYLATION; 2; HETEROARENES; H BONDS; 1,3-AZOLES; BENZAMIDES; CATALYST; ROUTE;

D O I：

10.1021/acs.orglett.7b02265

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Azolyl propanoic acid derivatives are frequently found in biologically active molecules and pharmaceuticals. Here, we report the oxidative heteroarylation of unactivated C(sp(3))-H bonds with azole C(sp(2))-H bonds via copper or nickel catalysis with the aid of removable bidentate auxiliary, which provides a rapid pathway to beta-azolyl propanoic acid derivatives. A variety of azoles such as oxazole, benzoxazole, thiazole, benzothiazoles, benzimidazole, purine, and even [1,2,4]triazolo[1,5-a]pyrimidine could be engaged

引用

页码：4830 / 4833

页数：4

共 29 条

[1] Nucleophilic Aryl Fluorination and Aryl Halide Exchange Mediated by a CuI/CuIII Catalytic Cycle [J].

Casitas, Alicia ;

Canta, Merce ;

Sola, Miquel ;

Costas, Miguel ;

Ribas, Xavi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (48) :19386-19392

[2]

Chai W., 2014, U.S. Patent, Patent No. 20140275028

[3] Nickel Catalysis Enables Oxidative C(sp2)-H/C(sp2)-H Cross-Coupling Reactions between Two Heteroarenes [J].

Cheng, Yangyang ;

Wu, Yimin ;

Tan, Guangyin ;

You, Jingsong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (40) :12275-12279

[4]

Chupak L. S., 2001, Patent Appl, Patent No. [WO 01/51487 Al, 0151487]

[5] ortho-Heteroarylation of Azobenzenes by Rh-Catalyzed Cross-Dehydrogenative Coupling: An Approach to Conjugated Biaryls [J].

Deng, Hong ;

Li, Hongji ;

Wang, Lei .

ORGANIC LETTERS, 2016, 18 (13) :3110-3113

[6] Rhodium or Ruthenium-Catalyzed Oxidative C?H/C?H Cross-Coupling: Direct Access to Extended p-Conjugated Systems [J].

Dong, Jiaxing ;

Long, Zhen ;

Song, Feijie ;

Wu, Ningjie ;

Guo, Qiang ;

Lan, Jingbo ;

You, Jingsong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :580-584

[7] An Enantioselective Oxidative C-H/C-H Cross-Coupling Reaction: Highly Efficient Method To Prepare Planar Chiral Ferrocenes [J].

Gao, De-Wei ;

Gu, Qing ;

You, Shu-Li .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (08) :2544-2547

[8]

Goldberg S., 2016, Patent Appl. US, Patent No. [2016/0120850 Al, 20160210850]

[9] Rhodium(III)-Catalyzed Oxidative C-H/C-H Cross-Coupling of Heteroarenes and Masked Benzylamines [J].

Hu, Jundie ;

Li, Guobao ;

Yuan, Chunchen ;

Huang, Zhi-Bin ;

Shi, Da-Qing ;

Zhao, Yingsheng .

ORGANIC LETTERS, 2016, 18 (23) :5998-6001

[10] Use of the Wilkinson Catalyst for the ortho-C-H Heteroarylation of Aromatic Amines: Facile Access to Highly Extended π-Conjugated Heteroacenes for Organic Semiconductors [J].

Huang, Yumin ;

Wu, Di ;

Huang, Jingsheng ;

Guo, Qiang ;

Li, Juan ;

You, Jingsong .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) :12158-12162

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