Literature DB >> 22296639

Visible-light-mediated utilization of α-aminoalkyl radicals: addition to electron-deficient alkenes using photoredox catalysts.

Yoshihiro Miyake1, Kazunari Nakajima, Yoshiaki Nishibayashi.   

Abstract

Synthetic use of α-aminoalkyl radicals formed by single electron oxidation of amines is quite limited. Here we demonstrate addition of α-aminoalkyl radicals to electron-deficient alkenes by visible-light-mediated electron transfer using transition metal polypyridyl complexes as photocatalysts, via a sequential redox pathway.

Entities:  

Year:  2012        PMID： 22296639     DOI： 10.1021/ja211770y

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  35 in total

1.  Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis.

Authors:  Laura Ruiz Espelt; Iain S McPherson; Eric M Wiensch; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2015-02-16       Impact factor: 15.419

2.  Photoredox-catalyzed Direct Reductive Amination of Aldehydes without an External Hydrogen/Hydride Source.

Authors:  Rauful Alam; Gary A Molander
Journal:  Org Lett       Date:  2018-04-13       Impact factor: 6.005

3.  Photoredox-Catalyzed Site-Selective α-C(sp3 )-H Alkylation of Primary Amine Derivatives.

Authors:  Melissa A Ashley; Chiaki Yamauchi; John C K Chu; Shinya Otsuka; Hideki Yorimitsu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-15       Impact factor: 15.336

Review 4.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

5.  Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis.

Authors:  Gerald Pratsch; Larry E Overman
Journal:  J Org Chem       Date:  2015-10-30       Impact factor: 4.354

6.  Detection of Fleeting Amine Radical Cations and Elucidation of Chain Processes in Visible-Light-Mediated [3 + 2] Annulation by Online Mass Spectrometric Techniques.

Authors:  Yi Cai; Jiang Wang; Yuexiang Zhang; Zhi Li; David Hu; Nan Zheng; Hao Chen
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

7.  Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization.

Authors:  Morgan M Walker; Brian Koronkiewicz; Shuming Chen; K N Houk; James M Mayer; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419

8.  Transition metal photoredox catalysis of radical thiol-ene reactions.

Authors:  Elizabeth L Tyson; Michael S Ament; Tehshik P Yoon
Journal:  J Org Chem       Date:  2012-11-12       Impact factor: 4.354

9.  Brønsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across Michael acceptors.

Authors:  Laura Ruiz Espelt; Eric M Wiensch; Tehshik P Yoon
Journal:  J Org Chem       Date:  2013-04-10       Impact factor: 4.354

10.  A visible-light-mediated oxidative C-N bond formation/aromatization cascade: photocatalytic preparation of N-arylindoles.

Authors:  Soumitra Maity; Nan Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-22       Impact factor: 15.336
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