Metal-Free Photochemical C-Se Cross-Coupling of Aryl Halides with Diselenides

被引：15

作者：

Wang, Ruizhe ^{[1
]}

Wang, Xinyu ^{[2
]}

Mao, Shuai ^{[2
]}

Zhao, Yahao ^{[2
]}

Yuan, Bo ^{[2
]}

Yang, Xue-Yan ^{[2
]}

Li, Jianjun ^{[1
]}

Chen, Zhengkai ^{[3
]}

机构：

[1] Xi An Jiao Tong Univ, Sch Chem, MOE Key Lab Nonequilibrium Synth & Modulat Conden, Xian 710049, Shaanxi, Peoples R China

[2] Xi An Jiao Tong Univ, Sch Pharm, Dept Med Chem, Xian 710061, Shaanxi, Peoples R China

[3] Zhejiang Sci Tech Univ, Dept Chem, Key Lab Surface & Interface Sci Polymer Mat Zheji, Hangzhou 310018, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 09期

基金：

中国博士后科学基金; 中国国家自然科学基金;

关键词：

Aryl halides; Diselenides; Photochemistry; Radical reactions; C-Se bond coupling; DIARYL SELENIDES; DIPHENYL DISELENIDE; CATALYZED SYNTHESIS; CLEAVAGE; IODIDE; BORYLATION; DISULFIDE; CHEMISTRY; ANALOGS;

D O I：

10.1002/adsc.202200042

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A light-mediated C-Se bond coupling reaction of aryl halides with diselenides under mild photocatalyst-free conditions for preparing aryl selenoethers has been achieved. The transformation is charactered by readily available materials, mild conditions, broad substrate scope and high efficiency. A reasonable mechanism has been proposed based on the preliminary mechanistic investigation. The protocol is also suitable for forging C-S bond and C-Te bond by the use of disulfides and ditellurides.

引用

页码：1607 / 1612

页数：6

共 70 条

[51] Reduced species (HSO2-,SO2•-) promoted one-pot efficient synthesis of phenyl alkyl selenides
Tang Ri-Yuan
Zhong Ping
Lin Qiu-Lian
[J]. CHINESE JOURNAL OF CHEMISTRY, 2007, 25 (04) : 558 - 561
[52] Magnesium-induced copper-catalyzed synthesis of unsymmetrical diaryl chalcogenide compounds from aryl iodide via cleavage of the Se-Se or S-S bond
Taniguchi, N
Onami, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) : 915 - 920
[53] Identification and quantitation of seleno-amino acids in mung bean sprouts by high-performance liquid chromatography coupled with mass spectrometry (HPLC-MS)
Tie, Mei
Sun, Jifeng
Gao, Yu
Yao, Yi
Wang, Tingting
Zhong, Honglu
Li, Huawei
[J]. EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 2018, 244 (03) : 491 - 500
[54] Tuning radical reactivity for selective radical/radical cross-coupling
Wang, Shengchun
Tang, Shan
Lei, Aiwen
[J]. SCIENCE BULLETIN, 2018, 63 (15) : 1006 - 1009
[55] 3-(3,4,5-Trimethoxyphenylselenyl)-1H-indoles and their selenoxides as combretastatin A-4 analogs: Microwave-assisted synthesis and biological evaluation
Wen, Zhiyong
Xu, Jingwen
Wang, Zhiwei
Qi, Huan
Xu, Qile
Bai, Zhaoshi
Zhang, Qian
Bao, Kai
Wu, Yingling
Zhang, Weige
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 : 184 - 194
[56] Cu-Mediated arylselenylation of aryl halides with trifluoromethyl aryl selenonium ylides
Wu, Shuai
Shi, Jin
Zhang, Cheng-Pan
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (32) : 7468 - 7473
[57] Involving Single-Atom Silver(0) in Selective Dehalogenation by AgF under Visible-Light Irradiation
Wu, Wenli
Cui, Enxin
Zhang, Yun
Zhang, Chen
Zhu, Feng
Tung, Chen-Ho
Wang, Yifeng
[J]. ACS CATALYSIS, 2019, 9 (07) : 6335 - 6341
[58] Surface Modification Based on Diselenide Dynamic Chemistry: Towards Liquid Motion and Surface Bioconjugation
Xia, Jiahao
Zhao, Peng
Zheng, Ke
Lu, Chenjie
Yin, Shouchun
Xu, Huaping
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (02) : 542 - 546
[59] Radicals: Reactive Intermediates with Translational Potential
Yan, Ming
Lo, Julian C.
Edwards, Jacob T.
Baran, Phil S.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (39) : 12692 - 12714
[60] K2S2O8-promoted C-Se bond formation to construct α-phenylseleno carbonyl compounds and α,β-unsaturated carbonyl compounds
Yang, Xue-Yan
Wang, Ruizhe
Wang, Lu
Li, Jianjun
Mao, Shuai
Zhang, San-Qi
Chen, Nanzheng
[J]. RSC ADVANCES, 2020, 10 (48) : 28902 - 28905

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