Literature DB >> 24432711

Continuous flow α-trifluoromethylation of ketones by metal-free visible light photoredox catalysis.

David Cantillo1, Oscar de Frutos, Juan A Rincón, Carlos Mateos, C Oliver Kappe.   

Abstract

A continuous-flow, two-step procedure for the preparation of α-CF3-substituted carbonyl compounds has been developed. The carbonyl substrates were converted in situ into the corresponding silyl enol ethers, mixed with the CF3 radical source, and then irradiated with visible light using a flow reactor based on transparent tubing and a household compact fluorescent lamp. The continuous protocol uses Eosin Y as an inexpensive photoredox catalyst and requires only 20 min to complete the two reaction steps.

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Year:  2014        PMID: 24432711     DOI: 10.1021/ol403650y

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


  6 in total

1.  Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.

Authors:  Mohammad B Khaled; Roukaya K El Mokadem; Jimmie D Weaver
Journal:  J Am Chem Soc       Date:  2017-09-08       Impact factor: 15.419

2.  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

3.  Micro-flow nanocatalysis: synergic effect of TfOH@SPIONs and micro-flow technology as an efficient and robust catalytic system for the synthesis of plasticizers.

Authors:  Maryam Tashi; Behnaz Shafiee; Yoshie Sakamaki; Ji-Yun Hu; Zachary Heidrick; Ahmad R Khosropour; M Hassan Beyzavi
Journal:  RSC Adv       Date:  2018-11-13       Impact factor: 3.361

4.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation and chlorination. Part 2: Use of CF3SO2Cl.

Authors:  Hélène Chachignon; Hélène Guyon; Dominique Cahard
Journal:  Beilstein J Org Chem       Date:  2017-12-19       Impact factor: 2.883

5.  Discovery and mechanistic study of a photocatalytic indoline dehydrogenation for the synthesis of elbasvir.

Authors:  Hatice G Yayla; Feng Peng; Ian K Mangion; Mark McLaughlin; Louis-Charles Campeau; Ian W Davies; Daniel A DiRocco; Robert R Knowles
Journal:  Chem Sci       Date:  2015-12-07       Impact factor: 9.825

6.  3D designed and printed chemical generators for on demand reagent synthesis.

Authors:  Sergey S Zalesskiy; Philip J Kitson; Przemyslaw Frei; Andrius Bubliauskas; Leroy Cronin
Journal:  Nat Commun       Date:  2019-12-02       Impact factor: 14.919

  6 in total

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