Literature DB >> 31588452

Photocatalytic hydroacylation of trifluoromethyl alkenes.

Pei Fan1, Chang Zhang1, Yun Lan1, Zhiyang Lin1, Linchuan Zhang1, Chuan Wang1.   

Abstract

Hydrofunctionalization of trifluoromethyl alkenes is highly challenging, because the nucleophilic addition is oftentimes followed by β-F elimination in this case. By the use of tetrabutylammonium decatungstate (TBADT) as a hydrogen-atom-transfer (HAT) photocatalyst for acyl C-H activation, we successfully avoid the β-F elimination in the hydroacylation of trifluoromethyl alkenes with aldehydes. This light (390 nm) promoted reaction provides a facile and efficient access to various β-CF3 ketones in complete regiocontrol with high functionality tolerance and 100% atom economy.

Entities:  

Year:  2019        PMID: 31588452     DOI: 10.1039/c9cc07285c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  5 in total

Review 1.  Visible Light-Induced Transition Metal Catalysis.

Authors:  Kelvin Pak Shing Cheung; Sumon Sarkar; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 72.087

2.  Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones.

Authors:  Shi-Chao Ren; Xing Yang; Bivas Mondal; Chengli Mou; Weiyi Tian; Zhichao Jin; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2022-05-23       Impact factor: 17.694

3.  Photoredox-mediated hydroalkylation and hydroarylation of functionalized olefins for DNA-encoded library synthesis.

Authors:  Shorouk O Badir; Alexander Lipp; Matthias Krumb; María Jesús Cabrera-Afonso; Lisa Marie Kammer; Victoria E Wu; Minxue Huang; Adam Csakai; Lisa A Marcaurelle; Gary A Molander
Journal:  Chem Sci       Date:  2021-08-05       Impact factor: 9.825

4.  Bromine radical as a visible-light-mediated polarity-reversal catalyst.

Authors:  Han Wang; Haiwang Liu; Mu Wang; Meirong Huang; Xiangcheng Shi; Tonglin Wang; Xu Cong; Jianming Yan; Jie Wu
Journal:  iScience       Date:  2021-06-05

Review 5.  Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622

  5 in total

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