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Literature DB >> 26797782

Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis.

Jian Rong¹, Ling Deng¹, Ping Tan¹, Chuanfa Ni², Yucheng Gu³, Jinbo Hu⁴.

Abstract

The radical fluoroalkylation of isocyanides with fluorinated sulfones is enabled by visible-light photoredox catalysis. A wide range of readily available mono-, di-, and trifluoromethyl heteroaryl sulfones can thus be used as efficient radical fluoroalkylation reagents under mild conditions. This method not only describes a new synthetic application of fluorinated sulfones, but also provides a new route to fluoroalkyl radicals.

Entities: Chemical

Keywords: fluorine; isocyanides; photoredox catalysis; radical reactions; sulfones

Year: 2016 PMID： 26797782 DOI： 10.1002/anie.201510533

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

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Cited

14 in total

1. Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification.

Authors: Rory C McAtee; Joel W Beatty; Christopher C McAtee; Corey R J Stephenson
Journal: Org Lett Date: 2018-06-01 Impact factor: 6.005

2. Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.

Authors: Johnny W Lee; Sanghyun Lim; Daniel N Maienshein; Peng Liu; Ming-Yu Ngai
Journal: Angew Chem Int Ed Engl Date: 2020-09-24 Impact factor: 15.336

3. Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

Authors: Zhichao Lu; Olivia Hennis; Joseph Gentry; Bo Xu; Gerald B Hammond
Journal: Org Lett Date: 2020-05-13 Impact factor: 6.005

4. Direct Conversion of Nitriles into Alkene "Isonitriles".

Authors: Yajun Li; Fraser F Fleming
Journal: Angew Chem Int Ed Engl Date: 2016-10-25 Impact factor: 15.336

5. Catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes to versatile enantioenriched-fluoroalkyl amines.

Authors: Jin-Shun Lin; Fu-Li Wang; Xiao-Yang Dong; Wei-Wei He; Yue Yuan; Su Chen; Xin-Yuan Liu
Journal: Nat Commun Date: 2017-03-23 Impact factor: 14.919

Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis.

1. Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification.

2. Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.

3. Base-Promoted Radical Azofluoromethylation of Unactivated Alkenes.

4. Direct Conversion of Nitriles into Alkene "Isonitriles".

5. Catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes to versatile enantioenriched-fluoroalkyl amines.

Review 6. Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review.

7. Late-Stage ¹⁸ F-Difluoromethyl Labeling of N-Heteroaromatics with High Molar Activity for PET Imaging.

Review 8. Progress in Difluoroalkylation of Organic Substrates by Visible Light Photoredox Catalysis.

9. Direct C-H difluoromethylation of heterocycles via organic photoredox catalysis.

10. Metal-free tandem carbene N-H insertions and C-C bond cleavages.