Literature DB >> 29939456

Brønsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C-C Bond Formation via Amidyl Radicals.

Jiaqi Jia1, Yee Ann Ho1, Raoul F Bülow1, Magnus Rueping1,2.   

Abstract

The synthesis of alkyne- and alkene-decorated lactams has been achieved through a photoredox-initiated radical cascade reaction. The developed Brønsted base assisted, photoredox-catalyzed, intramolecular 5-exo-trig cyclization/intermolecular radical addition/elimination reaction provides facile access to functionalized γ-lactams, with good functional group tolerance and high yields.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Brønsted base; lactam derivatives; photoredox catalysis; proton-coupled electron transfer (PCET); radical reactions; sulfonyl radical

Year:  2018        PMID： 29939456     DOI： 10.1002/chem.201802907

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


  7 in total

1.  Transition State Asymmetry in C-H Bond Cleavage by Proton-Coupled Electron Transfer.

Authors:  Julia W Darcy; Scott S Kolmar; James M Mayer
Journal:  J Am Chem Soc       Date:  2019-06-27       Impact factor: 15.419

2.  Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations.

Authors:  Feiyang Xu; Scott A Shuler; Donald A Watson
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-19       Impact factor: 15.336

Review 3.  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

Review 4.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

5.  Enantioselective Michael-Proton Transfer-Lactamization for Pyroglutamic Acid Derivatives: Synthesis of Dimethyl-(S,E)-5-oxo-3-styryl-1-tosylpyrrolidine-2,2-dicarboxylate.

Authors:  Christian M Chaheine; Conner J Song; Paul T Gladen; Daniel Romo
Journal:  Organic Synth       Date:  2021

Review 6.  Alkynylation of radicals: spotlight on the "Third Way" to transfer triple bonds.

Authors:  Franck Le Vaillant; Jérôme Waser
Journal:  Chem Sci       Date:  2019-08-13       Impact factor: 9.825

7.  Photoredox-catalyzed aminofluorosulfonylation of unactivated olefins.

Authors:  Tao Zhong; Ji-Tao Yi; Zhi-Da Chen; Quan-Can Zhuang; Yong-Zhao Li; Gui Lu; Jiang Weng
Journal:  Chem Sci       Date:  2021-06-07       Impact factor: 9.825
  7 in total

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