Photoredox/Copper Dual-Catalyzed Phosphorothiolation of Propargylic Derivatives for the Switchable Synthesis of S-Alkyl, S-Vinyl and S-Allenyl Phosphorothioates

被引：1

作者：

Shi, Shanshan ^{[1
]}

Chen, Hu ^{[1
]}

Yang, Shiwei ^{[1
]}

Dong, Huaze ^{[1
]}

Zhu, Jinmiao ^{[1
]}

Zheng, Bin ^{[1
]}

Wang, Xiaohong ^{[1
]}

Liang, Zhaoyang ^{[1
]}

Ren, Hongyu ^{[1
]}

Gao, Yuzhen ^{[2
]}

机构：

[1] Hefei Normal Univ, Dept Chem & Pharmaceut Engn, Hefei 230061, Anhui, Peoples R China

[2] Chinese Acad Sci, Fujian Inst Res Struct Matter, Ctr Excellence Mol Synth, State Key Lab Struct Chem,Fujian Sci & Technol Inn, Fuzhou 350002, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 33期

基金：

中国国家自然科学基金;

关键词：

CROSS-COUPLINGS; SUBSTITUTION; REAGENTS; ALCOHOLS; SULFUR;

D O I：

10.1021/acs.orglett.4c02636

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a photoredox/copper dual-catalyzed selective phosphorothiolation of propargylic derivatives from easily accessible [P(O)SH] compounds. This reaction provides a general, mild and versatile procedure to synthesize a variety of synthetically useful S-alkyl, S-vinyl and S-allenyl phosphorothioates selectively from the same set of simple starting materials.

引用

页码：7049 / 7054

页数：6

共 5 条

[1] Synthesis of S-Aryl Phosphorothioates by Copper-Catalyzed Phosphorothiolation of Diaryliodonium and Arenediazonium Salts
Zhang, Liangliang
Zhang, Pengbo
Li, Xueqin
Xu, Jian
Tang, Guo
Zhao, Yufen
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13): : 5588 - 5594
[2] Iron-catalyzed alkoxyl radical-mediated C-C bond cleavage/phosphorothiolation: a new approach to functionalized S-alkyl phosphorothioates
Bai, Ming
Liu, Shuai
Xin, Hong
Yang, Xu
Duan, Xin-Hua
Guo, Li-Na
ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (28) : 5855 - 5860
[3] Copper and Photocatalytic Radical Relay Enabling Fluoroalkylphosphorothiolation of Alkenes: Modular Synthesis of Fluorine-Containing S-Alkyl Phosphorothioates and Phosphorodithioates
Zhang, Pengbo
Li, Wenwu
Qu, Weilong
Shu, Zhigang
Tao, Yingjun
Lin, Jinming
Gao, Xia
ORGANIC LETTERS, 2021, 23 (23) : 9267 - 9272
[4] One-pot copper nanoparticle-catalyzed synthesis of S-aryl- and S-vinyl dithiocarbamates in water: high diastereoselectivity achieved for vinyl dithiocarbamates
Bhadra, Sukalyan
Saha, Amit
Ranu, Brindaban C.
GREEN CHEMISTRY, 2008, 10 (11) : 1224 - 1230
[5] Synthesis, characterization and antimicrobial activity of copper(II) complexes with some S-alkyl derivatives of thiosalicylic acid. Crystal structure of the binuclear copper(II) complex with S-methyl derivative of thiosalicylic acid
Nikolic, Milos V.
Mijajlovic, Marina Z.
Jevtic, Verica V.
Ratkovic, Zoran R.
Radojevic, Ivana D.
Comic, Ljiljana R.
Novakovic, Sladana B.
Bogdanovic, Goran A.
Trifunovic, Srecko R.
Radic, Gordana P.
POLYHEDRON, 2014, 79 : 80 - 87

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