Metal-Free Visible-Light-Mediated Oxidative Cross-Coupling of Thiols with P(O)H Compounds Using Air as the Oxidant

被引：127

作者：

Sun, Jian-Guo ^{[1
]}

Yang, Hua ^{[1
]}

Li, Ping ^{[1
]}

Zhang, Bo ^{[1
]}

机构：

[1] China Pharmaceut Univ, State Key Lab Nat Med, 24 Tongjia Xiang, Nanjing 210009, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 19期

关键词：

SECONDARY PHOSPHINE OXIDES; C-H ARYLATION; PHOTOREDOX CATALYSIS; SINGLET OXYGEN; PROMOTED SYNTHESIS; NICKEL CATALYSIS; ARYL; PHOSPHONATES; THIOPHOSPHATES; AMINES;

D O I：

10.1021/acs.orglett.6b02563

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Visible light along with 5 mol % of rose bengal, catalyzes the direct S-P(O) coupling between thiols and P(O) H compounds in the presence of air as the green oxidant. The, protocol is operationally simple and amenable to gram-scale synthesis. A variety of S-P(O) coupling products can be readily. prepared in moderate to excellent yields. The reaction features good functional-group tolerance, operational simplicity, and excellent practicality.

引用

页码：5114 / 5117

页数：4

共 50 条

[41] Intraligand Charge Transfer Enables Visible-Light-Mediated Nickel-Catalyzed Cross-Coupling Reactions
Cavedon, Cristian
Gisbertz, Sebastian
Reischauer, Susanne
Vogl, Sarah
Sperlich, Eric
Burke, John H.
Wallick, Rachel F.
Schrottke, Stefanie
Hsu, Wei-Hsin
Anghileri, Lucia
Pfeifer, Yannik
Richter, Noah
Teutloff, Christian
Mueller-Werkmeister, Henrike
Cambie, Dario
Seeberger, Peter H.
Vura-Weis, Josh
van der Veen, Renske M.
Thomas, Arne
Pieber, Bartholomaus
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (46)
[42] Metal-Free Catalyst for Visible-Light-Induced Oxidation of Unactivated Alcohols Using Air/Oxygen as an Oxidant
Schilling, Waldemar
Riemer, Daniel
Zhang, Yu
Hatami, Nareh
Das, Shoubhik
ACS CATALYSIS, 2018, 8 (06): : 5425 - 5430
[43] Visible-Light-Mediated Synthesis of Rutaecarpine Alkaloids through C-N Cross-Coupling Reaction
Chen, Dong
Li, Shiqing
Wang, Jinhua
Gou, Tiantian
Zhang, Linfeng
Wang, Guixia
Kong, Xiangfei
SYNLETT, 2021, 32 (10) : 987 - 992
[44] Visible-Light-Mediated Aminoquinolate Diarylboron-Catalyzed Metal-Free Hydroxylation of Organoboronic Acids under Air and Room Temperature
Wei, Lanfeng
Zhang, Jinli
Xu, Liang
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (37) : 13894 - 13899
[45] Visible Light-Mediated Photocatalytic Metal-Free Cross-Coupling Reaction of Alkenyl Carboxylic Acids with Diarylphosphine Oxides Leading to β-Ketophosphine Oxides
Qian, Hai-Feng
Li, Cheng-Kun
Zhou, Zhi-Hao
Tao, Ze-Kun
Shoberu, Adedamola
Zou, Jian-Ping
ORGANIC LETTERS, 2018, 20 (18) : 5947 - 5951
[46] Transition metal-free visible light-mediated photocatalytic aerobic oxidative synthesis of N-heterocycles using molecular oxygen as an oxidant
Hu, Yongke
Tian, Hongyou
Cao, Haotian
Li, Jin
Li, Shaozhong
Li, Huaju
Li, Yanxing
Shen, Gulou
Chen, Lei
MOLECULAR CATALYSIS, 2024, 566
[47] Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen
Wei, Lanfeng
Wei, Yu
Zhang, Jinli
Xu, Liang
GREEN CHEMISTRY, 2021, 23 (12) : 4446 - 4450
[48] Oxidative metal-free cross-coupling of secondary phosphine chalcogenides and benzenediols: Synthesis of phosphinochalcogenoic O-diesters
Gusarova, Nina K.
Volkov, Pavel A.
Ivanova, Nina I.
Larina, Ludmila I.
Trofimov, Boris A.
HETEROATOM CHEMISTRY, 2012, 23 (04) : 322 - 328
[49] DBU-mediated metal-free oxidative cyanation of α-amino carbonyl compounds: using molecular oxygen as the oxidant
Li, Lei
Wang, Qian
Liu, Pei
Meng, Hua
Kan, Xing-Lan
Liu, Qun
Zhao, Yu-Long
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (01) : 165 - 171
[50] Visible-Light-Mediated Metal-Free Hydrosilylation of Alkenes through Selective Hydrogen Atom Transfer for Si-H Activation
Zhou, Rong
Goh, Yi Yiing
Liu, Haiwang
Tao, Hairong
Li, Lihua
Wu, Jie
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (52) : 16621 - 16625

← 1 2 3 4 5 →