Literature DB >> 28696124

Visible-Light-Triggered Directly Reductive Arylation of Carbonyl/Iminyl Derivatives through Photocatalytic PCET.

Ming Chen1, Xinxin Zhao1, Chao Yang1, Wujiong Xia1.   

Abstract

The first visible-light-mediated radical-radical cross-coupling strategy that enables the direct arylation of carbonyl/iminyl derivatives in the presence of Et3N has been realized. Such an atom-economical protocol furnishes a broad scope of arylation products such as secondary/tertiary alcohols and amines via a PCET process that facilitates the challenging reduction of C═X (X = O, N). Mechanistic investigation indicates two photocatalytic redox cycles were involved in the process, and Et3N was proved to serve as a dual reductant and proton donor. Moreover, the isolated byproducts and controlled experiments could be considered as powerful supporting evidence for our hypothesis.

Entities:  

Year:  2017        PMID: 28696124     DOI: 10.1021/acs.orglett.7b01677

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


  14 in total

1.  Direct Synthesis of Secondary Benzylic Alcohols Enabled by Photoredox/Ni Dual-Catalyzed Cross-Coupling.

Authors:  Rauful Alam; Gary A Molander
Journal:  J Org Chem       Date:  2017-11-27       Impact factor: 4.354

2.  Recent developments in transition-metal photoredox-catalysed reactions of carbonyl derivatives.

Authors:  Katarzyna N Lee; Ming-Yu Ngai
Journal:  Chem Commun (Camb)       Date:  2017-12-07       Impact factor: 6.222

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

4.  Reductive Arylation of Arylidene Malonates Using Photoredox Catalysis.

Authors:  Rick C Betori; Karl A Scheidt
Journal:  ACS Catal       Date:  2019-10-17       Impact factor: 13.700

5.  Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds.

Authors:  Shengfei Jin; Hang T Dang; Graham C Haug; Ru He; Viet D Nguyen; Vu T Nguyen; Hadi D Arman; Kirk S Schanze; Oleg V Larionov
Journal:  J Am Chem Soc       Date:  2020-01-10       Impact factor: 15.419

6.  Visible-light photoredox-catalyzed umpolung carboxylation of carbonyl compounds with CO2.

Authors:  Guang-Mei Cao; Xin-Long Hu; Li-Li Liao; Si-Shun Yan; Lei Song; Jason J Chruma; Li Gong; Da-Gang Yu
Journal:  Nat Commun       Date:  2021-06-03       Impact factor: 14.919

7.  Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions.

Authors:  Shrikant D Tambe; Kwan Hong Min; Naeem Iqbal; Eun Jin Cho
Journal:  Beilstein J Org Chem       Date:  2020-06-18       Impact factor: 2.883

Review 8.  Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis.

Authors:  Stephanie G E Amos; Marion Garreau; Luca Buzzetti; Jerome Waser
Journal:  Beilstein J Org Chem       Date:  2020-05-29       Impact factor: 2.883

9.  Visible light-promoted CO2 fixation with imines to synthesize diaryl α-amino acids.

Authors:  Xinyuan Fan; Xu Gong; Mengyue Ma; Rui Wang; Patrick J Walsh
Journal:  Nat Commun       Date:  2018-11-22       Impact factor: 14.919

10.  Photocatalytic reverse polarity Povarov reaction.

Authors:  Jamie A Leitch; Angel L Fuentes de Arriba; Joanne Tan; Oskar Hoff; Carlos M Martínez; Darren J Dixon
Journal:  Chem Sci       Date:  2018-07-06       Impact factor: 9.825

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