Literature DB >> 24272969

Visible-light-mediated decarboxylation/oxidative amidation of α-keto acids with amines under mild reaction conditions using O(2).

Jie Liu1, Qiang Liu, Hong Yi, Chu Qin, Ruopeng Bai, Xiaotian Qi, Yu Lan, Aiwen Lei.   

Abstract

Photochemistry has ushered in a new era in the development of chemistry, and photoredox catalysis has become a hot topic, especially over the last five years, with the combination of visible-light photoredox catalysis and radical reactions. A novel, simple, and efficient radical oxidative decarboxylative coupling with the assistant of the photocatalyst [Ru(phen)3 ]Cl2 is described. Various functional groups are well-tolerated in this reaction and thus provides a new approach to developing advanced methods for aerobic oxidative decarboxylation. The preliminary mechanistic studies revealed that: 1) an SET process between [Ru(phen)3 ](2+) * and aniline play an important role; 2) O2 activation might be the rate-determining step; and 3) the decarboxylation step is an irreversible and fast process.
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  amides; computational chemistry; photochemistry; reaction mechanism; synthetic methods

Mesh:

Substances:

Year:  2013        PMID: 24272969     DOI: 10.1002/anie.201308614

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  23 in total

1.  Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids.

Authors:  Lingling Chu; Jeffrey M Lipshultz; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-26       Impact factor: 15.336

2.  Visible-light-promoted decarboxylative radical cascade cyclization to acylated benzimidazo/indolo[2,1-a]isoquinolin-6(5H)-ones in water.

Authors:  Lili Tang; Yuejun Ouyang; Kai Sun; Bing Yu
Journal:  RSC Adv       Date:  2022-07-07       Impact factor: 4.036

3.  Acyl Radical Chemistry via Visible-Light Photoredox Catalysis.

Authors:  Arghya Banerjee; Zhen Lei; Ming-Yu Ngai
Journal:  Synthesis (Stuttg)       Date:  2018-12-12       Impact factor: 3.157

4.  Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids.

Authors:  Anna V Davies; Keegan P Fitzpatrick; Rick C Betori; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-24       Impact factor: 15.336

5.  Merging photoredox and nickel catalysis: decarboxylative cross-coupling of carboxylic acids with vinyl halides.

Authors:  Adam Noble; Stefan J McCarver; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2015-01-12       Impact factor: 15.419

6.  Sterically Demanding Oxidative Amidation of α-Substituted Malononitriles with Amines Using O2.

Authors:  Jing Li; Martin J Lear; Yujiro Hayashi
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-14       Impact factor: 15.336

7.  Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals.

Authors:  L Candish; M Freitag; T Gensch; F Glorius
Journal:  Chem Sci       Date:  2017-02-27       Impact factor: 9.825

8.  Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation.

Authors:  Franck Le Vaillant; Matthew D Wodrich; Jérôme Waser
Journal:  Chem Sci       Date:  2016-12-22       Impact factor: 9.825

9.  Installing amino acids and peptides on N-heterocycles under visible-light assistance.

Authors:  Yunhe Jin; Min Jiang; Hui Wang; Hua Fu
Journal:  Sci Rep       Date:  2016-02-02       Impact factor: 4.379

10.  Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles.

Authors:  Wen Ding; Shaoyu Mai; Qiuling Song
Journal:  Beilstein J Org Chem       Date:  2015-11-11       Impact factor: 2.883

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