Literature DB >> 27137478

Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction.

Lu Li1,2, Xiaoyue Mu1, Wenbo Liu1, Yichen Wang2, Zetian Mi2, Chao-Jun Li1.   

Abstract

We describe a simple, metal- and oxidant-free photochemical strategy for the direct trifluoromethylation of unactivated arenes and heteroarenes under either ultraviolet or visible light irradiation. We demonstrated that photoexcited aliphatic ketones, such as acetone and diacetyl, can be used as promising low-cost radical initiators to generate CF3 radicals from sodium triflinate efficiently. The broad utility of this strategy and its benefit to medicinal chemistry are demonstrated by the direct trifluoromethylation of unprotected bidentate chelating ligand, xanthine alkaloids, nucleosides, and related antiviral drug molecules.

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Year:  2016        PMID: 27137478     DOI: 10.1021/jacs.6b02782

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  21 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

2.  Laser-Initiated Radical Trifluoromethylation of Peptides and Proteins: Application to Mass-Spectrometry-Based Protein Footprinting.

Authors:  Ming Cheng; Bojie Zhang; Weidong Cui; Michael L Gross
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-05       Impact factor: 15.336

3.  Aqueous Benzylic C-H Trifluoromethylation for Late-Stage Functionalization.

Authors:  Shuo Guo; Deyaa I AbuSalim; Silas P Cook
Journal:  J Am Chem Soc       Date:  2018-09-24       Impact factor: 15.419

4.  The past, present, and future of the Yang reaction.

Authors:  Chuo Chen
Journal:  Org Biomol Chem       Date:  2016-08-12       Impact factor: 3.876

5.  Versatile Open-Source Photoreactor Architecture for Photocatalysis Across the Visible Spectrum.

Authors:  Philip P Lampkin; Blaise J Thompson; Samuel H Gellman
Journal:  Org Lett       Date:  2021-06-23       Impact factor: 6.072

6.  Visible-light-induced aerobic C3-H fluoroalkoxylation of quinoxalin-2(1H)-ones with fluoroalkyl alcohols.

Authors:  Xiaobo Xu; Chengcai Xia; Xiaojun Li; Jian Sun; Liqiang Hao
Journal:  RSC Adv       Date:  2020-01-09       Impact factor: 4.036

Review 7.  Radicals: Reactive Intermediates with Translational Potential.

Authors:  Ming Yan; Julian C Lo; Jacob T Edwards; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

8.  CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na.

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

9.  Selective Radical Trifluoromethylation of Native Residues in Proteins.

Authors:  Mateusz Imiołek; Gogulan Karunanithy; Wai-Lung Ng; Andrew J Baldwin; Véronique Gouverneur; Benjamin G Davis
Journal:  J Am Chem Soc       Date:  2018-01-22       Impact factor: 15.419

10.  A cross-dehydrogenative C(sp3)-H heteroarylation via photo-induced catalytic chlorine radical generation.

Authors:  Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal:  Nat Commun       Date:  2021-06-29       Impact factor: 14.919

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