Literature DB >> 31638821

Visible-Light-Induced Deaminative Thioesterification of Amino Acid Derived Katritzky Salts via Electron Donor-Acceptor Complex Formation.

Mingcheng Yang1, Tianpeng Cao1, Tianxiao Xu1, Saihu Liao1,2.   

Abstract

A visible-light-mediated deaminative thioesterification of amino acid derived Katritzky salts with thiobenzoic acid has been developed, which provides a novel synthetic method for the synthesis of α-mercapto acid derivatives under mild conditions. This photoredox catalyst-free generation of alkyl radicals via C-N bond cleavage is enabled by the formation of an electron-donor-acceptor (EDA) complex between the Katritzky salt and thiobenzoic acid anion, which represents a new entry for EDA complex chemistry.

Entities:  

Year:  2019        PMID: 31638821     DOI: 10.1021/acs.orglett.9b03284

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


  10 in total

Review 1.  Recent Progress in Fragmentation of Katritzky Salts Enabling Formation of C-C, C-B, and C-S Bonds.

Authors:  Yuan Gao; Songwei Jiang; Nian-Dong Mao; Huan Xiang; Ji-Long Duan; Xiang-Yang Ye; Li-Wei Wang; Yang Ye; Tian Xie
Journal:  Top Curr Chem (Cham)       Date:  2022-05-19

2.  α-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines.

Authors:  Kristen M Baker; Amanda Tallon; Richard P Loach; Olivia P Bercher; Matthew A Perry; Mary P Watson
Journal:  Org Lett       Date:  2021-09-27       Impact factor: 6.072

3.  A practical and sustainable two-component Minisci alkylation via photo-induced EDA-complex activation.

Authors:  Mohammed Sharique; Jadab Majhi; Roshan K Dhungana; Lisa Marie Kammer; Matthias Krumb; Alexander Lipp; Eugénie Romero; Gary A Molander
Journal:  Chem Sci       Date:  2022-04-26       Impact factor: 9.969

4.  Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes.

Authors:  Giacomo E M Crisenza; Daniele Mazzarella; Paolo Melchiorre
Journal:  J Am Chem Soc       Date:  2020-03-12       Impact factor: 15.419

Review 5.  Leveraging of Sulfur Anions in Photoinduced Molecular Transformations.

Authors:  Haoyu Li; Yuliang Liu; Shunsuke Chiba
Journal:  JACS Au       Date:  2021-10-20

6.  A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones.

Authors:  Tsukasa Tanaka; Takehiro Kiuchi; Yuuki Ooe; Hajime Iwamoto; Shin-Ya Takizawa; Shigeru Murata; Eietsu Hasegawa
Journal:  ACS Omega       Date:  2022-01-26

7.  Divergent reactivity of sulfinates with pyridinium salts based on one- versus two-electron pathways.

Authors:  Myojeong Kim; Euna You; Seongjin Park; Sungwoo Hong
Journal:  Chem Sci       Date:  2021-03-31       Impact factor: 9.825

8.  Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines.

Authors:  Soniya Rani; Soumya Ranjan Dash; Asish Bera; Md Nirshad Alam; Kumar Vanka; Pradip Maity
Journal:  Chem Sci       Date:  2021-05-28       Impact factor: 9.825

9.  Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts.

Authors:  David Schönbauer; Carlo Sambiagio; Timothy Noël; Michael Schnürch
Journal:  Beilstein J Org Chem       Date:  2020-04-21       Impact factor: 2.883

10.  A General Organocatalytic System for Electron Donor-Acceptor Complex Photoactivation and Its Use in Radical Processes.

Authors:  Eduardo de Pedro Beato; Davide Spinnato; Wei Zhou; Paolo Melchiorre
Journal:  J Am Chem Soc       Date:  2021-07-28       Impact factor: 15.419

  10 in total

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