Literature DB >> 23094660

Transition metal photoredox catalysis of radical thiol-ene reactions.

Elizabeth L Tyson1, Michael S Ament, Tehshik P Yoon.   

Abstract

We describe the anti-Markovnikov hydrothiolation of olefins using visible-light-absorbing transition metal photocatalysts. The key thiyl radical intermediates are generated upon quenching of photoexcited Ru*(bpz)3(2) with a variety of thiols. The adducts of a wide variety of olefins and thiols are formed in excellent yield (73-99%).

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Year:  2012        PMID： 23094660      PMCID： PMC3573243          DOI： 10.1021/jo3020825

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  44 in total

1.  Chalcogenides as organocatalysts.

Authors:  Eoghan M McGarrigle; Eddie L Myers; Ona Illa; Michael A Shaw; Samantha L Riches; Varinder K Aggarwal
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

2.  Photoredox catalysis with visible light.

Authors:  Kirsten Zeitler
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Visible Light Photocatalysis of Radical Anion Hetero-Diels-Alder Cycloadditions.

Authors:  Anna E Hurtley; Megan A Cismesia; Michael A Ischay; Tehshik P Yoon
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

4.  Photocatalyzed sulfide oxygenation with water as the unique oxygen atom source.

Authors:  Pascal Guillo; Olivier Hamelin; Pinar Batat; Gediminas Jonusauskas; Nathan D McClenaghan; Stéphane Ménage
Journal:  Inorg Chem       Date:  2012-02-01       Impact factor: 5.165

5.  Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

Authors:  Hui-Wen Shih; Mark N Vander Wal; Rebecca L Grange; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

6.  Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-05-02       Impact factor: 15.419

7.  1,2-Thio group migration in Rh(II) carbene reactions.

Authors:  Feng Xu; Weifeng Shi; Jianbo Wang
Journal:  J Org Chem       Date:  2005-05-13       Impact factor: 4.354

8.  Convenient synthesis of unsymmetrical organochalcogenides using organoboronic acids with dichalcogenides via cleavage of the S-S, Se-Se, or Te-Te bond by a copper catalyst.

Authors:  Nobukazu Taniguchi
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

9.  Photoreversible patterning of biomolecules within click-based hydrogels.

Authors:  Cole A DeForest; Kristi S Anseth
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-08       Impact factor: 15.336

10.  Asymmetric synthesis of tertiary thiols and thioethers.

Authors:  Jonathan Clayden; Paul Maclellan
Journal:  Beilstein J Org Chem       Date:  2011-05-10       Impact factor: 2.883
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  20 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

2.  Palladium-catalysed construction of butafulvenes.

Authors:  Xin Huang; Bing-Zhi Chen; Pengbin Li; Ding-Wei Ji; Jinxian Liu; Hao Zheng; Sa-Na Yang; Yan-Cheng Hu; Boshun Wan; Xiang-Ping Hu; Chunling Fu; Yankai Huang; Jian Zheng; Qing-An Chen; Shengming Ma
Journal:  Nat Chem       Date:  2022-08-18       Impact factor: 24.274

3.  Anti-Markovnikov hydroamination of alkenes catalyzed by an organic photoredox system.

Authors:  Tien M Nguyen; David A Nicewicz
Journal:  J Am Chem Soc       Date:  2013-06-19       Impact factor: 15.419

4.  A general strategy for organocatalytic activation of C-H bonds via photoredox catalysis: direct arylation of benzylic ethers.

Authors:  Katrine Qvortrup; Danica A Rankic; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2013-12-27       Impact factor: 15.419

5.  Evolution of a Synthetic Strategy for Complex Polypyrrole Alkaloids: Total Syntheses of Curvulamine and Curindolizine.

Authors:  Jun Xuan; Karl T Haelsig; Michael Sheremet; Paulo A Machicao; Thomas J Maimone
Journal:  J Am Chem Soc       Date:  2021-02-11       Impact factor: 15.419

6.  An improved procedure for the preparation of Ru(bpz)3(PF6)2 via a high-yielding synthesis of 2,2'-bipyrazine.

Authors:  Danielle M Schultz; James W Sawicki; Tehshik P Yoon
Journal:  Beilstein J Org Chem       Date:  2015-01-14       Impact factor: 2.883

7.  Activation of C-H bonds via the merger of photoredox and organocatalysis: a coupling of benzylic ethers with Schiff bases.

Authors:  Dominik Hager; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-12-02       Impact factor: 15.419

8.  Three-Component Azidation of Styrene-Type Double Bonds: Light-Switchable Behavior of a Copper Photoredox Catalyst.

Authors:  Gabriele Fumagalli; Pauline T G Rabet; Scott Boyd; Michael F Greaney
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-26       Impact factor: 15.336

9.  Redox mediators in visible light photocatalysis: photocatalytic radical thiol-ene additions.

Authors:  Elizabeth L Tyson; Zachary L Niemeyer; Tehshik P Yoon
Journal:  J Org Chem       Date:  2014-01-27       Impact factor: 4.354

Review 10.  Photocatalytic formation of carbon-sulfur bonds.

Authors:  Alexander Wimmer; Burkhard König
Journal:  Beilstein J Org Chem       Date:  2018-01-05       Impact factor: 2.883
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