Literature DB >> 31904244

NHC-Catalyzed Radical Trifluoromethylation Enabled by Togni Reagent.

Bei Zhang1, Qiupeng Peng1, Donghui Guo1, Jian Wang1.   

Abstract

An unprecedented carbene-catalyzed radical trifluoromethylation of olefins with aldehydes in the presence of Togni reagent was developed, thus providing the β-trifluoromethyl-α-substituted ketones with a broad scope and moderate to high chemical yields. Notably, this process includes a single-electron-transfer process and utilizes the persistent N-heterocyclic-carbene-bound radical as a key intermediate to trigger the cascade radical cross-coupling.

Entities:  

Year:  2020        PMID: 31904244     DOI: 10.1021/acs.orglett.9b04203

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


  11 in total

1.  Single-electron Carbene Catalysis in Redox Processes.

Authors:  Anna V Bay; Karl A Scheidt
Journal:  Trends Chem       Date:  2022-02-11

2.  Three-component carboacylation of alkenes via cooperative nickelaphotoredox catalysis.

Authors:  Dingyi Wang; Lutz Ackermann
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

3.  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

4.  Photoinduced Trifluoromethylation with CF3Br as a Trifluoromethyl Source: Synthesis of α-CF3-Substituted Ketones.

Authors:  Ransong Ma; Zhoubin Deng; Ke-Hu Wang; Junjiao Wang; Danfeng Huang; Yingpeng Su; Yulai Hu; Xiaobo Lv
Journal:  ACS Omega       Date:  2022-04-12

5.  Critical Assessment of the Reducing Ability of Breslow-type Derivatives and Implications for Carbene-Catalyzed Radical Reactions*.

Authors:  Ludivine Delfau; Samantha Nichilo; Florian Molton; Julie Broggi; Eder Tomás-Mendivil; David Martin
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-15       Impact factor: 16.823

6.  Suzuki-type cross-coupling of alkyl trifluoroborates with acid fluoride enabled by NHC/photoredox dual catalysis.

Authors:  Hua Huang; Qing-Song Dai; Hai-Jun Leng; Qing-Zhu Li; Si-Lin Yang; Ying-Mao Tao; Xiang Zhang; Ting Qi; Jun-Long Li
Journal:  Chem Sci       Date:  2022-01-21       Impact factor: 9.825

7.  NHC and visible light-mediated photoredox co-catalyzed 1,4-sulfonylacylation of 1,3-enynes for tetrasubstituted allenyl ketones.

Authors:  Lihong Wang; Ruiyang Ma; Jiaqiong Sun; Guangfan Zheng; Qian Zhang
Journal:  Chem Sci       Date:  2022-02-10       Impact factor: 9.825

8.  Desymmetrization of N-Cbz glutarimides through N-heterocyclic carbene organocatalysis.

Authors:  Zhouli Hu; Chenlong Wei; Qianqian Shi; Xianfang Hong; Jinhua Liu; Xiangui Zhou; Jinna Han; Wei Cao; Ashis Kumar Gupta; Xiaoxiang Zhang; Donghui Wei; Zhenqian Fu; Wei Huang
Journal:  Nat Commun       Date:  2022-07-13       Impact factor: 17.694

Review 9.  Recent advances in N-heterocyclic carbene-based radical catalysis.

Authors:  Takuya Ishii; Kazunori Nagao; Hirohisa Ohmiya
Journal:  Chem Sci       Date:  2020-05-11       Impact factor: 9.825

10.  Light-Driven Carbene Catalysis for the Synthesis of Aliphatic and α-Amino Ketones.

Authors:  Anna V Bay; Keegan P Fitzpatrick; Gisela A González-Montiel; Abdikani Omar Farah; Paul Ha-Yeon Cheong; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-14       Impact factor: 16.823

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