Eosin-Y-Catalyzed Photoredox C-S Bond Formation: Easy Access to Thioethers

被引：29

作者：

Chand, Shiv ^{[1
]}

Pandey, Anand Kumar ^{[1
]}

Singh, Rahul ^{[1
]}

Kumar, Saurabh ^{[1
]}

Singh, Krishna Nand ^{[1
]}

机构：

[1] Banaras Hindu Univ, Dept Chem, Ctr Adv Study, Inst Sci, Varanasi 221005, Uttar Pradesh, India

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2019年 / 14卷 / 24期

关键词：

Eosin Y; hydrazones; photoredox catalysis; sulfenylation; thioethers; CROSS-COUPLING REACTIONS; METAL-FREE; EFFICIENT SYNTHESIS; NICKEL-CATALYST; ARYL HALIDES; THIOLS; DERIVATIVES; HYDRAZONES; PALLADIUM; ARYLATION;

D O I：

10.1002/asia.201901060

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An operationally simple Eosin Y catalyzed sulfenylation of hydrazones has been realized to afford a range of thioethers under visible light. The methodology provides high yields of thioethers under ambient conditions employing readily available and inexpensive starting materials. The reaction has broad substrate scope and is compatible with various functional groups.

引用

页码：4712 / 4716

页数：5

共 68 条

[31] Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation [J].

Hu, Xiao-Qiang ;

Qi, Xiaotian ;

Chen, Jia-Rong ;

Zhao, Quan-Qing ;

Wei, Qiang ;

Lan, Yu ;

Xiao, Wen-Jing .

NATURE COMMUNICATIONS, 2016, 7

[32] Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers [J].

Ichiishi, Naoko ;

Malapit, Christian A. ;

Wozniak, Lukasz ;

Sanford, Melanie S. .

ORGANIC LETTERS, 2018, 20 (01) :44-47

[33] Data-Mining for Sulfur and Fluorine: An Evaluation of Pharmaceuticals To Reveal Opportunities for Drug Design and Discovery [J].

Ilardi, Elizabeth A. ;

Vitaku, Edon ;

Njardarson, Jon T. .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (07) :2832-2842

[34] Copper-Catalyzed Stereospecific C-S Coupling Reaction of Enantioenriched Tertiary Benzylic Amines via in Situ Activation with Methyl Triflate [J].

Jiang, Wenlong ;

Li, Nutao ;

Zhou, Lihong ;

Zeng, Qingle .

ACS CATALYSIS, 2018, 8 (11) :9899-+

[35] Viracept (nelfinavir mesylate, AG1343): A potent, orally bioavailable inhibitor of HIV-1 protease [J].

Kaldor, SW ;

Kalish, VJ ;

Davies, JF ;

Shetty, BV ;

Fritz, JE ;

Appelt, K ;

Burgess, JA ;

Campanale, KM ;

Chirgadze, NY ;

Clawson, DK ;

Dressman, BA ;

Hatch, SD ;

Khalil, DA ;

Kosa, MB ;

Lubbehusen, PP ;

Muesing, MA ;

Patick, AK ;

Reich, SH ;

Su, KS ;

Tatlock, JH .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (24) :3979-3985

[36] Visible light organophotoredox catalysis: a general approach to β-keto sulfoxidation of alkenes [J].

Keshari, Twinkle ;

Yadav, Vinod K. ;

Srivastava, Vishnu P. ;

Yadav, Lal Dhar S. .

GREEN CHEMISTRY, 2014, 16 (08) :3986-3992

[37] Catalytic Enantioselective Formation of C-C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update [J].

Kobayashi, Shu ;

Mori, Yuichiro ;

Fossey, John S. ;

Salter, Matthew M. .

CHEMICAL REVIEWS, 2011, 111 (04) :2626-2704

[38] Oxidoreductive coupling of thiols with aryl halides catalyzed by copper on iron [J].

Kovacs, Szabolcs ;

Novak, Zoltan .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) :711-716

[39] Palladium-Catalyzed C-S Coupling: Access to Thioethers, Benzo[b]thiophenes, and Thieno[3,2-b]thiophenes [J].

Kuhn, Marius ;

Falk, Florian C. ;

Paradies, Jan .

ORGANIC LETTERS, 2011, 13 (15) :4100-4103

[40] A general, efficient, and inexpensive catalyst system for the coupling of aryl iodides and thiols [J].

Kwong, FY ;

Buchwald, SL .

ORGANIC LETTERS, 2002, 4 (20) :3517-3520

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