Synthesis of aryl sulfides via radical-radical cross coupling of electron-rich arenes using visible light photoredox catalysis

被引：5

作者：

Das, Amrita ^{[1
]}

Maity, Mitasree ^{[1
]}

Malcherek, Simon ^{[1
]}

Koenig, Burkhard ^{[1
]}

Rehbein, Julia ^{[1
]}

机构：

[1] Univ Regensburg, Inst Organ Chem, Dept Chem & Pharm, Univ Str 31, D-93053 Regensburg, Germany

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 14卷

关键词：

arenes; oxidation; photocatalysis; thiolation; visible light; S BOND FORMATION; C-S; CHARGE-TRANSFER; SUBSTITUTED BENZOTHIAZOLES; MILD CONDITIONS; BORONIC ACIDS; FACILE ACCESS; THIOLS; DISULFIDES; SULFUR;

D O I：

10.3762/bjoc.14.228

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electron-rich arenes react with aryl and alkyl disulfides in the presence of catalytic amounts of [Ir(dF(CF3)ppy)(2)(dtbpy)]PF6 and (NH4)(2)S2O8 under blue light irradiation to yield arylthiols. The reaction proceeds at room temperature and avoids the use of prefunctionalized arenes. Experimental evidence suggests a radical-radical cross coupling mechanism.

引用

页码：2520 / 2528

页数：9

共 50 条

[1] Direct C(sp3)-H difluoromethylation via radical-radical cross-coupling by visible-light photoredox catalysis
Xiong, Wei
Qin, Wen-Bing
Zhao, Ya-Shi
Fu, Kai-Zhong
Liu, Guo-Kai
Organic Chemistry Frontiers, 2022, 9 (08) : 2141 - 2148
[2] Direct C(sp3)-H difluoromethylation via radical-radical cross-coupling by visible-light photoredox catalysis
Xiong, Wei
Qin, Wen-Bing
Zhao, Ya-Shi
Fu, Kai-Zhong
Liu, Guo-Kai
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (08): : 2141 - 2148
[3] Asymmetric Radical-Radical Cross-Coupling through Visible-Light-Activated Iridium Catalysis
Wang, Chuanyong
Qin, Jie
Shen, Xiaodong
Riedel, Radostan
Harms, Klaus
Meggers, Eric
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (02) : 685 - 688
[4] Direct C-H Phosphonylation of Electron-Rich Arenes and Heteroarenes by Visible-Light Photoredox Catalysis
Shaikh, Rizwan S.
Ghosh, Indrajit
Koenig, Burkhard
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) : 12120 - 12124
[5] Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis
Hu, Xiao-Qiang
Liu, Zi-Kui
Xiao, Wen-Jing
CATALYSTS, 2020, 10 (09) : 1 - 26
[6] Acyl Radical Chemistry via Visible-Light Photoredox Catalysis
Banerjee, Arghya
Lei, Zhen
Ngai, Ming-Yu
SYNTHESIS-STUTTGART, 2019, 51 (02): : 303 - 333
[7] Efficient 11C-Cyanation of Electron-Rich Arenes via Organic Photoredox Catalysis
Wu, Xuedan
Chen, Wei
Douglas, Natalie
Bida, Gerald
Tu, Xianshuang
Ma, Xinrui
Wu, Zhanhong
Nicewicz, David
Li, Zibo
JOURNAL OF NUCLEAR MEDICINE, 2023, 64
[8] Potent Reductants via Electron-Primed Photoredox Catalysis: Unlocking Aryl Chlorides for Radical Coupling
Cowper, Nicholas G. W.
Chernowsky, Colleen P.
Williams, Oliver P.
Wickens, Zachary K.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (05) : 2093 - 2099
[9] Photoredox-catalyzed three-component carbotrifluoromethylation of alkenes via radical-radical cross-coupling
Tang, Lin
Lv, Ge
Wu, Taijun
Zhang, Lufang
Wang, Xiaoyu
Jia, Fengjuan
Zhou, Qiuju
Zou, Guodong
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (17): : 4708 - 4715
[10] Radical Fluoroalkylation of Aryl Alkenes with Fluorinated Sulfones by Visible- Light Photoredox Catalysis
Rong Jian
Ni Chuanfa
Wang Yunze
Kuang Cuiwen
Gu Yucheng
Hu Jinbo
ACTA CHIMICA SINICA, 2017, 75 (01) : 105 - 109

← 1 2 3 4 5 →