Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts

被引:29
作者
Chen, Guang-Le [1 ,2 ]
He, Shi-Hui [1 ,2 ]
Cheng, Liang [1 ,2 ]
Liu, Feng [1 ,2 ,3 ]
机构
[1] Soochow Univ, Coll Pharmaceut Sci, Jiangsu Key Lab Neuropsychiat Dis, Suzhou 215123, Jiangsu, Peoples R China
[2] Soochow Univ, Coll Pharmaceut Sci, Dept Med Chem, Suzhou 215123, Jiangsu, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
关键词
SULFUR;
D O I
10.1021/acs.orglett.1c03075
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We herein report a selective and catalytic C(sp(3))-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp(3))-H sulfonylation and thiolation and also exhibits good functional group tolerance.
引用
收藏
页码:8338 / 8342
页数:5
相关论文
共 37 条
[1]  
Baldwin, 1993, N S SULFONES ORGANIC, V10
[2]   Copper-catalyzed remote C(sp3)-H azidation and oxidative trifluoromethylation of benzohydrazides [J].
Bao, Xu ;
Wang, Qian ;
Zhu, Jieping .
NATURE COMMUNICATIONS, 2019, 10 (1)
[3]   THE INVENTION OF RADICAL REACTIONS .17. A DECARBOXYLATIVE SULFONYLATION OF CARBOXYLIC-ACIDS [J].
BARTON, DHR ;
LACHER, B ;
MISTERKIEWICZ, B ;
ZARD, SZ .
TETRAHEDRON, 1988, 44 (04) :1153-1158
[4]   Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3•OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates [J].
Cao, Liang ;
Luo, Shi-He ;
Jiang, Kai ;
Hao, Zhi-Feng ;
Wang, Bo-Wen ;
Pang, Chu-Ming ;
Wang, Zhao-Yang .
ORGANIC LETTERS, 2018, 20 (16) :4754-4758
[5]   Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides [J].
Dong, Dao-Qing ;
Han, Qing-Qing ;
Yang, Shao-Hui ;
Song, Jing-Cheng ;
Li, Na ;
Wang, Zu-Li ;
Xu, Xin-Ming .
CHEMISTRYSELECT, 2020, 5 (42) :13103-13134
[6]   Iron-Catalyzed, Fluoroamide-Directed C-H Fluorination [J].
Groendyke, Brian J. ;
AbuSalim, Deyaa I. ;
Cook, Silas P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) :12771-12774
[7]   A New Avenue toward Androgen Receptor Pan-antagonists: C2 Sterically Hindered Substitution of Hydroxy-propanamides [J].
Guerrini, Andrea ;
Tesei, Anna ;
Ferroni, Claudia ;
Paganelli, Giulia ;
Zamagni, Alice ;
Carloni, Silvia ;
Di Donato, Marzia ;
Castoria, Gabriella ;
Leonetti, Carlo ;
Porru, Manuela ;
De Cesare, Michelandrea ;
Zaffaroni, Nadia ;
Beretta, Giovanni Luca ;
Del Rio, Alberto ;
Varchi, Greta .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (17) :7263-7279
[8]   Catalytic Decarboxylative Radical Sulfonylation [J].
He, Jiayan ;
Chen, Guangle ;
Zhang, Benxiang ;
Li, Yi ;
Chen, Jia-Rong ;
Xiao, Wen-Jing ;
Liu, Feng ;
Li, Chaozhong .
CHEM, 2020, 6 (05) :1149-1159
[9]   Recent Advances in the Catalytic Synthesis of Arylsulfonyl Compounds [J].
Joseph, Devaneyan ;
Idris, Muhammad Aliyu ;
Chen, Jiajia ;
Lee, Sunwoo .
ACS CATALYSIS, 2021, 11 (07) :4169-4204
[10]   USE OF SAMARIUM DIIODIDE AS AN ALTERNATIVE TO SODIUM MERCURY AMALGAM IN THE JULIA-LYTHGOE OLEFINATION [J].
KECK, GE ;
SAVIN, KA ;
WEGLARZ, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3194-3204