Literature DB >> 26888456

Alkyne Difunctionalization by Dual Gold/Photoredox Catalysis.

Adrian Tlahuext-Aca1, Matthew N Hopkinson1, R Aleyda Garza-Sanchez1, Frank Glorius2.   

Abstract

Highly selective tandem nucleophilic addition/cross-coupling reactions of alkynes have been developed using visible-light-promoted dual gold/photoredox catalysis. The simultaneous oxidation of Au(I) and coordination of the coupling partner by photo-generated aryl radicals, and the use of catalytically inactive gold precatalysts allows for high levels of selectivity for the cross-coupled products without competing hydrofunctionalization or homocoupling. As demonstrated in representative arylative Meyer-Schuster and hydration reactions, this work expands the scope of dual gold/photoredox catalysis to the largest class of substrates for gold catalysts and benefits from the mild and environmentally attractive nature of visible-light activation.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; arylation; diazonium salts; gold; synthetic methods

Year:  2016        PMID: 26888456     DOI: 10.1002/chem.201600710

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  14 in total

1.  Catalytic Alkyne Arylation Using Traceless Directing Groups.

Authors:  Jung-Woo Park; Bubwoong Kang; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-11       Impact factor: 15.336

2.  Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant.

Authors:  Jin Wang; Chiyu Wei; Xuming Li; Pengyi Zhao; Chuan Shan; Lukasz Wojtas; Hao Chen; Xiaodong Shi
Journal:  Chemistry       Date:  2020-04-14       Impact factor: 5.236

3.  Highly Efficient and Stereoselective Thioallylation of Alkynes: Possible Gold Redox Catalysis with No Need for a Strong Oxidant.

Authors:  Jin Wang; Shuyao Zhang; Chang Xu; Lukasz Wojtas; Novruz G Akhmedov; Hao Chen; Xiaodong Shi
Journal:  Angew Chem Int Ed Engl       Date:  2018-05-07       Impact factor: 15.336

4.  Gold Redox Catalysis through Base-Initiated Diazonium Decomposition toward Alkene, Alkyne, and Allene Activation.

Authors:  Boliang Dong; Haihui Peng; Stephen E Motika; Xiaodong Shi
Journal:  Chemistry       Date:  2017-07-24       Impact factor: 5.236

5.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

Review 6.  Dual Catalysis Strategies in Photochemical Synthesis.

Authors:  Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal:  Chem Rev       Date:  2016-04-25       Impact factor: 60.622

7.  Dual gold and photoredox catalysed C-H activation of arenes for aryl-aryl cross couplings.

Authors:  V Gauchot; D R Sutherland; A-L Lee
Journal:  Chem Sci       Date:  2017-01-27       Impact factor: 9.825

8.  Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes.

Authors:  Haoyu Li; Cuicui Shan; Chen-Ho Tung; Zhenghu Xu
Journal:  Chem Sci       Date:  2017-01-04       Impact factor: 9.825

Review 9.  Photoredox Catalysis Unlocks Single-Electron Elementary Steps in Transition Metal Catalyzed Cross-Coupling.

Authors:  Mark D Levin; Suhong Kim; F Dean Toste
Journal:  ACS Cent Sci       Date:  2016-05-03       Impact factor: 14.553

10.  Merging Visible Light Photoredox Catalysis with Metal Catalyzed C-H Activations: On the Role of Oxygen and Superoxide Ions as Oxidants.

Authors:  David C Fabry; Magnus Rueping
Journal:  Acc Chem Res       Date:  2016-08-24       Impact factor: 22.384

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