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Literature DB >> 23380942

Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis.

Yusuke Yasu¹, Takashi Koike, Munetaka Akita.

Abstract

A facile synthesis of trifluoromethylated alkenes by the radical-mediated trifluoromethylation of vinyltrifluoroborates has been developed. Togni's reagent serves as a CF(3) radical precursor in the presence of the photoredox catalyst [Ru(bpy)(3)](PF(6))(2) under visible light irradiation. This new photocatalytic protocol can be applicable to a wide variety of vinylborates containing electronically diverse substituents and hetero-aromatics.

Entities: Chemical

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Year: 2013 PMID： 23380942 DOI： 10.1039/c3cc39235j

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

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Cited

14 in total

1. Julia-Kocienski Approach to Trifluoromethyl-Substituted Alkenes^1.

Authors: Deborah O Ayeni; Samir K Mandal; Barbara Zajc
Journal: Tetrahedron Lett Date: 2013-11-06 Impact factor: 2.415

2. Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters.

Authors: Alexander M Haydl; John F Hartwig
Journal: Org Lett Date: 2019-02-14 Impact factor: 6.005

3. Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one.

Authors: Nico Santschi; Roman C Sarott; Elisabeth Otth; Reinhard Kissner; Antonio Togni
Journal: Beilstein J Org Chem Date: 2014-01-02 Impact factor: 2.883

4. Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.

Authors: Yahui Wang; Adam Noble; Christopher Sandford; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2017-01-18 Impact factor: 15.336

5. Mechanisms and applications of cyclometalated Pt(ii) complexes in photoredox catalytic trifluoromethylation.

Authors: Won Joon Choi; Sungkyu Choi; Kei Ohkubo; Shunichi Fukuzumi; Eun Jin Cho; Youngmin You
Journal: Chem Sci Date: 2014-11-24 Impact factor: 9.825

6. Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters.

Authors: Adam Noble; Riccardo S Mega; Daniel Pflästerer; Eddie L Myers; Varinder K Aggarwal
Journal: Angew Chem Int Ed Engl Date: 2018-01-26 Impact factor: 15.336

Visible-light-induced synthesis of a variety of trifluoromethylated alkenes from potassium vinyltrifluoroborates by photoredox catalysis.

1. Julia-Kocienski Approach to Trifluoromethyl-Substituted Alkenes^1.

2. Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters.

3. Synthesis, characterization and initial evaluation of 5-nitro-1-(trifluoromethyl)-3H-1λ(3),2-benziodaoxol-3-one.

4. Enantiospecific Trifluoromethyl-Radical-Induced Three-Component Coupling of Boronic Esters with Furans.

5. Mechanisms and applications of cyclometalated Pt(ii) complexes in photoredox catalytic trifluoromethylation.

6. Visible-Light-Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ-Amino Boronic Esters.

Review 7. Radical-Induced 1,2-Migrations of Boron Ate Complexes.

Review 8. Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

9. Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent.

10. Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis.