Literature DB >> 27978669

Thiophenol-Catalyzed Visible-Light Photoredox Decarboxylative Couplings of N-(Acetoxy)phthalimides.

Yunhe Jin1, Haijun Yang1, Hua Fu1.   

Abstract

We have developed visible-light photoredox decarboxylative couplings of N-(acetoxy)phthalimides without an added photocatalyst in which simple and commercially available thiophenols are used as the effective organocatalysts, and 4-(trifluoromethyl)thiophenol shows optimal catalytic activity. Three representative decarboxylative examples were chosen including one amination and two C-C bond couplings to confirm efficacy of the visible-light photoredox reactions, and the results exhibited that they performed very well at room temperature. The interesting discovery should provide a novel and environmentally friendly strategy for visible-light photoredox transformation of organic molecules.

Entities:  

Year:  2016        PMID: 27978669     DOI: 10.1021/acs.orglett.6b03300

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement.

Authors:  Wei Zhao; Ryan P Wurz; Jonas C Peters; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

2.  Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

Authors:  Jing-Yu Guo; Ze-Yu Zhang; Ting Guan; Lei-Wen Mao; Qian Ban; Kai Zhao; Teck-Peng Loh
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

3.  Facile Conversion of α-Amino Acids into α-Amino Phosphonates by Decarboxylative Phosphorylation using Visible-Light Photocatalysis.

Authors:  Dominik Reich; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-04       Impact factor: 16.823

4.  Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: synthesis of diverse nitrogenous heterocyclic compounds.

Authors:  Guanglong Pan; Qian Yang; Wentao Wang; Yurong Tang; Yunfei Cai
Journal:  Beilstein J Org Chem       Date:  2021-05-17       Impact factor: 2.883

5.  Olefination of Alkyl Halides with Aldehydes by Merging Visible-Light Photoredox Catalysis and Organophosphorus Chemistry.

Authors:  Min Jiang; Haijun Yang; Quentin Lefebvre; Jihu Su; Hua Fu
Journal:  iScience       Date:  2018-07-20
  5 in total

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