Literature DB >> 24863669

Combining photoredox-catalyzed trifluoromethylation and oxidation with DMSO: facile synthesis of α-trifluoromethylated ketones from aromatic alkenes.

Ren Tomita1, Yusuke Yasu, Takashi Koike, Munetaka Akita.   

Abstract

Trifluoromethylated ketones are useful building blocks for organic compounds with a trifluoromethyl group. A new and facile synthesis of ketones with a trifluoromethyl substituent in the α-position proceeds through a one-pot photoredox-catalyzed trifluoromethylation-oxidation sequence of aromatic alkenes. Dimethyl sulfoxide (DMSO) serves as a key and mild oxidant under these photocatalytic conditions. Furthermore, an iridium photocatalyst, fac[Ir(ppy)3 ] (ppy=2-phenylpyridine), turned out to be crucial for the present photoredox process.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbocations; fluorine; homogeneous catalysis; oxidation; photochemistry

Year:  2014        PMID: 24863669     DOI: 10.1002/anie.201403590

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


  16 in total

1.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

Review 2.  Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors:  Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal:  Chem Rev       Date:  2021-10-08       Impact factor: 60.622

3.  Fluorine-decoupled carbon spectroscopy for the determination of configuration at fully substituted, trifluoromethyl- and perfluoroalkyl-bearing carbons: comparison with 19F-1H heteronuclear Overhauser effect spectroscopy.

Authors:  Appi Reddy Mandhapati; Takayuki Kato; Takahiko Matsushita; Bashar Ksebati; Andrea Vasella; Erik C Böttger; David Crich
Journal:  J Org Chem       Date:  2015-01-20       Impact factor: 4.354

4.  Iodine(III) Reagents in Radical Chemistry.

Authors:  Xi Wang; Armido Studer
Journal:  Acc Chem Res       Date:  2017-06-21       Impact factor: 22.384

5.  Redox-Neutral Dual Functionalization of Electron-Deficient Alkenes.

Authors:  Fredrik Pettersson; Giulia Bergonzini; Carlo Cassani; Carl-Johan Wallentin
Journal:  Chemistry       Date:  2017-05-10       Impact factor: 5.236

6.  Dual gold and photoredox catalysis: visible light-mediated intermolecular atom transfer thiosulfonylation of alkenes.

Authors:  Haoyu Li; Cuicui Shan; Chen-Ho Tung; Zhenghu Xu
Journal:  Chem Sci       Date:  2017-01-04       Impact factor: 9.825

7.  Trifluoroethoxy-Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low-Energy Red-Light Irradiation.

Authors:  Kohei Matsuzaki; Tomoya Hiromura; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2017-02-21       Impact factor: 2.911

8.  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

9.  Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols.

Authors:  Yusuke Arai; Ren Tomita; Gaku Ando; Takashi Koike; Munetaka Akita
Journal:  Chemistry       Date:  2015-12-16       Impact factor: 5.236

10.  Visible-light-induced oxidant and metal-free dehydrogenative cascade trifluoromethylation and oxidation of 1,6-enynes with water.

Authors:  Sadhan Jana; Ajay Verma; Rahul Kadu; Sangit Kumar
Journal:  Chem Sci       Date:  2017-07-10       Impact factor: 9.825

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