Literature DB >> 24571334

Vicinal difunctionalization of alkenes: chlorotrifluoromethylation with CF3SO2Cl by photoredox catalysis.

Se Hwan Oh1, Yashwardhan R Malpani, Neul Ha, Young-Sik Jung, Soo Bong Han.   

Abstract

Photoredox-catalyzed vicinal chlorotrifluoromethylation of alkene is described. In the presence of Ru(Phen)3Cl2, CF3SO2Cl was used as a source for the CF3 radical and chloride ion under visible light irradiation. Various terminal and internal alkenes were transformed to their vicinal chlorotrifluoromethylated derivatives. Biologically active compounds were applied under the condition to obtain desired products, suggesting that the method could be feasible for late-stage modification in drug discovery.

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Year:  2014        PMID: 24571334     DOI: 10.1021/ol403716t

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


  13 in total

1.  Excited-State Copper Catalysis for the Synthesis of Heterocycles.

Authors:  Arghya Banerjee; Satavisha Sarkar; Jagrut A Shah; Nicoline C Frederiks; Emmanuel A Bazan-Bergamino; Christopher J Johnson; Ming-Yu Ngai
Journal:  Angew Chem Int Ed Engl       Date:  2021-12-07       Impact factor: 15.336

2.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

3.  Remote Radical Desaturation of Unactivated C-H Bonds in Amides.

Authors:  Yong Xia; Kalipada Jana; Armido Studer
Journal:  Chemistry       Date:  2021-10-08       Impact factor: 5.020

4.  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

5.  Product Control in Alkene Trifluoromethylation: Hydrotrifluoromethylation, Vinylic Trifluoromethylation, and Iodotrifluoromethylation using Togni Reagent.

Authors:  Hiromichi Egami; Yoshihiko Usui; Shintaro Kawamura; Sayoko Nagashima; Mikiko Sodeoka
Journal:  Chem Asian J       Date:  2015-06-16

6.  Reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis.

Authors:  Rick C Betori; Benjamin R McDonald; Karl A Scheidt
Journal:  Chem Sci       Date:  2019-02-06       Impact factor: 9.825

Review 7.  Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis.

Authors:  Rik H Verschueren; Wim M De Borggraeve
Journal:  Molecules       Date:  2019-06-05       Impact factor: 4.411

Review 8.  Difunctionalization of Alkenes and Alkynes via Intermolecular Radical and Nucleophilic Additions.

Authors:  Hongjun Yao; Wenfei Hu; Wei Zhang
Journal:  Molecules       Date:  2020-12-28       Impact factor: 4.411

9.  Characterizing Chain Processes in Visible Light Photoredox Catalysis.

Authors:  Megan A Cismesia; Tehshik P Yoon
Journal:  Chem Sci       Date:  2015-06-07       Impact factor: 9.825

10.  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

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