Literature DB >> 28530821

Exploring the Reducing Ability of Organic Dye (Acr+-Mes) for Fluorination and Oxidation of Benzylic C(sp3)-H Bonds under Visible Light Irradiation.

Ming Xiang1, Zhi-Kun Xin1, Bin Chen1, Chen-Ho Tung1, Li-Zhu Wu1.   

Abstract

The excellent oxidizing capability of acridinium-based organic dye (Acr+-Mes) is fully studied in photoredox catalysis. However, its reducing ability is always considered weak for organic transformation. The reducing ability of Acr+-Mes is developed by Selectfluor to achieve effective fluorination and oxidation of benzylic C(sp3)-H bonds under visible light irradiation, which is not available for the direct use of oxidizing ability of excited Acr+-Mes. Mechanistic insights provided strong evidence for the oxidative quenching of Acr+-Mes.

Entities:  

Year:  2017        PMID： 28530821     DOI： 10.1021/acs.orglett.7b01270

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


  8 in total

1.  Combined Photoredox/Enzymatic C-H Benzylic Hydroxylations.

Authors:  Rick C Betori; Catherine M May; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-26       Impact factor: 15.336

2.  Copper-Catalyzed Functionalization of Benzylic C-H Bonds with N-Fluorobenzenesulfonimide: Switch from C-N to C-F Bond Formation Promoted by a Redox Buffer and Brønsted Base.

Authors:  Joshua A Buss; Aristidis Vasilopoulos; Dung L Golden; Shannon S Stahl
Journal:  Org Lett       Date:  2020-07-29       Impact factor: 6.005

3.  C(sp3)-H methylation enabled by peroxide photosensitization and Ni-mediated radical coupling.

Authors:  Aristidis Vasilopoulos; Shane W Krska; Shannon S Stahl
Journal:  Science       Date:  2021-04-23       Impact factor: 47.728

Review 4.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

5.  Selective carboxylation of reactive benzylic C-H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system.

Authors:  Toshifumi Dohi; Shohei Ueda; Kosuke Iwasaki; Yusuke Tsunoda; Koji Morimoto; Yasuyuki Kita
Journal:  Beilstein J Org Chem       Date:  2018-05-16       Impact factor: 2.883

6.  Chiral acid-catalysed enantioselective C-H functionalization of toluene and its derivatives driven by visible light.

Authors:  Fuyuan Li; Dong Tian; Yifan Fan; Richmond Lee; Gang Lu; Yanli Yin; Baokun Qiao; Xiaowei Zhao; Ziwei Xiao; Zhiyong Jiang
Journal:  Nat Commun       Date:  2019-04-16       Impact factor: 14.919

7.  Visible light-induced direct α C-H functionalization of alcohols.

Authors:  Linbin Niu; Jiamei Liu; Xing-An Liang; Shengchun Wang; Aiwen Lei
Journal:  Nat Commun       Date:  2019-01-28       Impact factor: 14.919

8.  Synthesis of Xanthones, Thioxanthones and Acridones by a Metal-Free Photocatalytic Oxidation Using Visible Light and Molecular Oxygen.

Authors:  Alejandro Torregrosa-Chinillach; Rafael Chinchilla
Journal:  Molecules       Date:  2021-02-12       Impact factor: 4.411
  8 in total

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