Selective remote C-H sulfonylation of aminoquinolines with arylsulfonyl chlorides via copper catalysis

被引：141

作者：

Liang, Hong-Wen ^{[1
]}

Jiang, Kun ^{[1
]}

Ding, Wei ^{[1
]}

Yuan, Yi ^{[1
]}

Shuai, Li ^{[1
]}

Chen, Ying-Chun ^{[1
]}

Wei, Ye ^{[1
]}

机构：

[1] Third Mil Med Univ, Coll Pharm, Chongqing 400038, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 95期

关键词：

UNSYMMETRICAL DIARYL SULFONES; BOND FUNCTIONALIZATION; DIRECT ARYLATION; N-OXIDES; PALLADIUM; ARYL; ALKYLATION; C(SP(3))-H; ACIDS; C(SP(2))-H;

D O I：

10.1039/c5cc05527j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Copper-catalysed direct C-H bond sulfonylation of aminoquinolines using commercially available and inexpensive arylsulfonyl chlorides as the sulfonylation reagents is described. The reactions took place exclusively at the C5-H position of the quinoline rings and tolerated a wide spectrum of functional groups. Moreover, synthetic transformations of the sulfonylated products led to useful compounds.

引用

页码：16928 / 16931

页数：4

共 50 条

[41] Visible Light/Copper Catalysis-Enabled Arylation and Alkenylation of Phosphorothioates via Site-Selective C-H Thianthrenation
Guo, Guoju
Ma, Jie
Dong, Yuzhen
Wu, Qilong
Lv, Jian
Shi, Yongjia
Yang, Daoshan
ORGANIC LETTERS, 2024, 26 (39) : 8382 - 8388
[42] Spectroscopic Investigation of the Remote C-H Allylation of Amides via Photoredox and Nickel Dual Catalysis
Bourgois, Celine
De Kreijger, Simon
Xu, Bin
Tambar, Uttam K.
Troian-Gautier, Ludovic
SYNLETT, 2024, 35 (16) : 1893 - 1898
[43] Coordination strategy-induced selective C-H amination of 8-aminoquinolines
Yi, Hong
Chen, Hong
Bian, Changliang
Tang, Zilu
Singh, Atul K.
Qi, Xiaotian
Yue, Xiaoyu
Lan, Yu
Lee, Jyh-Fu
Lei, Aiwen
CHEMICAL COMMUNICATIONS, 2017, 53 (50) : 6736 - 6739
[44] Dual Copper- and Aldehyde-Catalyzed Transient C-H Sulfonylation of Benzylamines
Higham, Joe I.
Ma, Tsz-Kan
Bull, James A.
ORGANIC LETTERS, 2023, 25 (28) : 5285 - 5290
[45] Aliphatic C-H alkylation via photoredox catalysis
Morton, Carla
Choi, Gilbert
Zhu, Qilei
Knowles, Robert
Alexanian, Erik
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[46] Direct C-H Transformation via Iron Catalysis
Sun, Chang-Liang
Li, Bi-Jie
Shi, Zhang-Jie
CHEMICAL REVIEWS, 2011, 111 (03) : 1293 - 1314
[47] Non-directed copper-catalyzed regioselective C-H sulfonylation of phenothiazines
Liu, Caiyan
Shen, Yongli
Yuan, Kedong
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (20) : 5009 - 5013
[48] Amine-Catalyzed Copper-Mediated C-H Sulfonylation of Benzaldehydes via a Transient Imine Directing Group
Higham, Joe, I
Bull, James A.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (27)
[49] Palladium-Catalyzed Site-Selective C-H Sulfonylation via Aryl Thianthrenium Salts to Access Diarylsulfones
Ni, Chunjie
Liu, Jin-Ping
Zhang, Xiao-Xu
Wang, Zi-Yi
Liang, Zhanhang
Chen, Chen
Qiu, Di
JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (09): : 3279 - 3289
[50] Enantioselective Radical Trifluoromethylation of Benzylic C-H Bonds via Cooperative Photoredox and Copper Catalysis
Xu, Pin
Fan, Wenzheng
Chen, Pinhong
Liu, Guosheng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (30) : 13468 - 13474

← 1 2 3 4 5 →