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

被引：6

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 53 条

[1] Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent
Ajiki, K
Hirano, M
Tanaka, K
[J]. ORGANIC LETTERS, 2005, 7 (19) : 4193 - 4195
[2] Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides:: p-orientation in the polyarylthiolation of polyfluorobenzenes
Arisawa, Mieko
Suzuki, Takaaki
Ishikawa, Tomofumi
Yamaguchi, Masahiko
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) : 12214 - +
[3] Synthesis of CuO on mesoporous silica and its applications for coupling reactions of thiols with aryl iodides
Chen, Chin-Keng
Chen, Yan-Wun
Lin, Che-Hung
Lin, Hong-Ping
Lee, Chin-Fa
[J]. CHEMICAL COMMUNICATIONS, 2010, 46 (02) : 282 - 284
[4] Synthesis of Aryl Thioethers through the N-Chlorosuccinimide-Promoted Cross-Coupling Reaction of Thiols with Grignard Reagents
Cheng, Jun-Hao
Ramesh, Chintakunta
Kao, Hsin-Lun
Wang, Yu-Jen
Chan, Chien-Ching
Lee, Chin-Fa
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) : 10369 - 10374
[5] Iron-catalyzed S-arylation of thiols with aryl iodides
Correa, Arkaitz
Carril, Monica
Bolm, Carsten
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (15) : 2880 - 2883
[6] Iron-catalysed carbon-heteroatom and heteroatom-heteroatom bond forming processes
Correa, Arkaitz
Mancheno, Olga Garcia
Bolm, Carsten
[J]. CHEMICAL SOCIETY REVIEWS, 2008, 37 (06) : 1108 - 1117
[7] Thiyl Radicals in Organic Synthesis
Denes, Fabrice
Pichowicz, Mark
Povie, Guillaume
Renaud, Philippe
[J]. CHEMICAL REVIEWS, 2014, 114 (05) : 2587 - 2693
[8] Cu-Catalyzed Three-Component Synthesis of Substituted Benzothiazoles in Water
Deng, Hang
Li, Zhengkai
Ke, Fang
Zhou, Xiangge
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (16) : 4840 - 4843
[9] Mechanism of exciplex decay: The quantum yields and the rate constants of radical ion formation from exciplexes with partial charge transfer
Dogadkin, DN
Dolotova, EV
Soboleva, IV
Kuzmin, MG
Plyusnin, VF
Pozdnyakov, IP
Grivin, VP
Vauthey, E
Brodard, P
Nicolet, O
[J]. HIGH ENERGY CHEMISTRY, 2004, 38 (06) : 392 - 400
[10] Enzymatic Carbon-Sulfur Bond Formation in Natural Product Biosynthesis
Dunbar, Kyle L.
Scharf, Daniel H.
Litomska, Agnieszka
Hertweck, Christian
[J]. CHEMICAL REVIEWS, 2017, 117 (08) : 5521 - 5577

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