Copper-catalyzed thiolation of imidazo[1,2-a]pyridines with (hetero)aryl thiols using molecular oxygen

被引：34

作者：

Zheng, Zhishuo ^{[1
]}

Qi, Deyu ^{[1
]}

Shi, Lei ^{[2
]}

机构：

[1] S China Univ Technol, Sch Comp Sci & Engn, Guangzhou 510640, Guangdong, Peoples R China

[2] Guangdong Univ Educ, Dept Chem, Guangzhou 510640, Guangdong, Peoples R China

来源：

CATALYSIS COMMUNICATIONS | 2015年 / 66卷

关键词：

Copper-catalyzed; Thiolation; Imidazo[1,2-a]pyridines; (Hetero)aryl thiols; Molecular oxygen; S BOND FORMATION; P-ARYLTHIO CINNAMIDES; C-H BONDS; REGIOSELECTIVE SULFENYLATION; ANTAGONISTS; C-3;

D O I：

10.1016/j.catcom.2015.03.023

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new and facile copper-catalyzed thiolation of imidazo[1,2-a]pyridines with (hetero)aryl thiols was developed for the formation of C-S bond by using molecular oxygen as oxidant under base-free conditions. The presented protocol has provided the selective C-3 sulfenated products with good yield. A computational study was carried out by using the B3LYP density functional theory to elucidate the regioselectivity of C-2 and C-3. Calculation results indicated that the thiolation toward C-3 was easier and smoother, which was consistent with our experiment results. (C) 2015 Elsevier B.V. All rights reserved.

引用

页码：83 / 86

页数：4

共 50 条

[1] Copper-catalyzed C-N bond formation with imidazo[1,2-a]pyridines
Sun, Kai
Mu, Shiqiang
Liu, Zhenhua
Feng, Ranran
Li, Yali
Pang, Kui
Zhang, Bing
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (36) : 6655 - 6658
[2] Copper-Catalyzed Aerobic Oxidative Cyclization of Ketoxime Acetates with Pyridines for the Synthesis of Imidazo[1,2-a]pyridines
Ren, Zhi-Hui
Zhao, Mi-Na
Yi, Yukun
Wang, Yao-Yu
Guan, Zheng-Hui
[J]. SYNTHESIS-STUTTGART, 2016, 48 (12): : 1920 - 1926
[3] Copper-Catalyzed Multicomponent Reactions (MCRs) for Disulfenylation of Imidazo[1,2-a]pyridines Using Elemental Sulfur and Arylhalides and Intramolecular Cyclization of Haloinnidazo[1,2-a]pyridines
Semwal, Rashmi
Ravi, Chitrakar
Saxena, Soumya
Adimurthy, Subbarayappa
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (21): : 14151 - 14160
[4] Copper-Catalyzed Intermolecular Oxidative Cyclization of Haloalkynes: Synthesis of 2-Halo-substituted Imidazo[1,2-a]pyridines, Imidazo[1,2-a]pyrazines and Imidazo[1,2-a]pyrimidines
Gao, Yang
Yin, Meizhou
Wu, Wanqing
Huang, Huawen
Jiang, Huanfeng
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2263 - 2273
[5] Aerobic Iron(III)-Catalyzed Direct Thiolation of Imidazo[1,2-a]pyridine with Thiols
Qin, Ling
Wu, Hui-bin
Weng, Lidong
Shen, Qun
Chen, Huoji
[J]. SYNOPEN, 2020, 4 (02): : 17 - 22
[6] Copper-Catalyzed Selenylation of Imidazo[1,2-a]pyridines with Selenium Powder via a Radical Pathway
Sun, Pengfei
Jiang, Min
Wei, Wei
Min, Yuanyuan
Zhang, Wen
Li, Wanhui
Yang, Daoshan
Wang, Hua
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (06): : 2906 - 2913
[7] Copper-catalyzed three-component reaction to synthesize polysubstituted imidazo[1,2-a]pyridines
Zhou, Zitong
Luo, Danyang
Li, Guanrong
Yang, Zhongtao
Cui, Liao
Yang, Weiguang
[J]. RSC ADVANCES, 2022, 12 (31) : 20199 - 20205
[8] Regioselective Copper-Catalyzed Dicarbonylation of Imidazo[1,2-a]pyridines with N,N-Disubstituted Acetamide or Acetone: An Approach to 1,2-Diketones Using Molecular Oxygen
Wang, Changcheng
Lei, Sai
Cao, Hua
Qiu, Shuxian
Liu, Jingyun
Deng, Hao
Yan, Caijuan
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24): : 12725 - 12732
[9] Synthesis of Naphtho-Fused Imidazo[1,2-a]pyridines through Copper-Catalyzed Cascade Reactions
Saini, Hitesh Kumar
Kaswan, Pinku
Pericherla, Kasiviswanadharaju
Kumar, Anil
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (12) : 1380 - 1385
[10] Conversion of Pyridine to Imidazo[1,2-a]pyridines by Copper-Catalyzed Aerobic Dehydrogenative Cyclization with Oxime Esters
Huang, Huawen
Ji, Xiaochen
Tang, Xiaodong
Zhang, Min
Li, Xianwei
Jiang, Huanfeng
[J]. ORGANIC LETTERS, 2013, 15 (24) : 6254 - 6257

← 1 2 3 4 5 →