Literature DB >> 24251623

Copper-mediated radical trifluoromethylation of unsaturated potassium organotrifluoroborates.

Marc Presset1, Daniel Oehlrich, Frederik Rombouts, Gary A Molander.   

Abstract

Copper-mediated trifluoromethylation of unsaturated organotrifluoroborates with the Langlois reagent (NaSO2CF3) and TBHP allows the introduction of trifluoromethyl groups into a variety of organic substructures. The reactions are easy to set up, the conditions are mild and general, and the process provides access to trifluoromethylated alkynes, alkenes, arenes, and heteroarenes in fair to good yields.

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Year:  2013        PMID： 24251623      PMCID： PMC3886853          DOI： 10.1021/jo4023233

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  29 in total

1.  Copper-mediated oxidative trifluoromethylation of boronic acids.

Authors:  Lingling Chu; Feng-Ling Qing
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

Review 2.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

3.  A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen)CuR(F)].

Authors:  Nichole D Litvinas; Patrick S Fier; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-14       Impact factor: 15.336

4.  Oxidative trifluoromethylation of arylboronates with shelf-stable potassium (trifluoromethyl)trimethoxyborate.

Authors:  Bilal A Khan; Annette E Buba; Lukas J Goossen
Journal:  Chemistry       Date:  2012-01-11       Impact factor: 5.236

5.  Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent.

Authors:  Jun Xu; Dong-Fen Luo; Bin Xiao; Zhao-Jing Liu; Tian-Jun Gong; Yao Fu; Lei Liu
Journal:  Chem Commun (Camb)       Date:  2011-03-07       Impact factor: 6.222

6.  Copper-catalyzed trifluoromethylation of aryl and vinyl boronic acids with an electrophilic trifluoromethylating reagent.

Authors:  Tianfei Liu; Qilong Shen
Journal:  Org Lett       Date:  2011-04-07       Impact factor: 6.005

Review 7.  CF(3)-bearing aromatic and heterocyclic building blocks.

Authors:  Manfred Schlosser
Journal:  Angew Chem Int Ed Engl       Date:  2006-08-18       Impact factor: 15.336

8.  Photochemical generation of highly destabilized vinyl cations: the effects of alpha- and beta-trifluoromethyl versus alpha- and beta-methyl substituents.

Authors:  Kaj van Alem; Geerte Belder; Gerrit Lodder; Han Zuilhof
Journal:  J Org Chem       Date:  2005-01-07       Impact factor: 4.354

9.  Synthesis and minisci reactions of organotrifluoroborato building blocks.

Authors:  Marc Presset; Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  J Org Chem       Date:  2013-04-17       Impact factor: 4.354

10.  Practical method for the Cu-mediated trifluoromethylation of arylboronic acids with CF3 radicals derived from NaSO2CF3 and tert-butyl hydroperoxide (TBHP).

Authors:  Yingda Ye; Stefan A Künzi; Melanie S Sanford
Journal:  Org Lett       Date:  2012-09-17       Impact factor: 6.005
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2.  Copper(i) reagent-promoted hydroxytrifluoromethylation of enamides: flexible synthesis of substituted-3-hydroxy-2-aryl-3-(2,2,2-trifluoro-1-arylethyl)isoindolin-1-one.

Authors:  Qing Wang; Peng Shi; Runsheng Zeng
Journal:  RSC Adv       Date:  2018-07-19       Impact factor: 4.036

3.  Academia-industry symbiosis in organic chemistry.

Authors:  Quentin Michaudel; Yoshihiro Ishihara; Phil S Baran
Journal:  Acc Chem Res       Date:  2015-02-23       Impact factor: 22.384

4.  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

5.  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

Review 6.  Indolylboronic Acids: Preparation and Applications.

Authors:  Marek Čubiňák; Tereza Edlová; Peter Polák; Tomáš Tobrman
Journal:  Molecules       Date:  2019-09-28       Impact factor: 4.411

7.  Copper-catalyzed chemoselective synthesis of 4-trifluoromethyl pyrazoles.

Authors:  Jiaqing Lu; Yuning Man; Yabin Zhang; Bo Lin; Qi Lin; Zhiqiang Weng
Journal:  RSC Adv       Date:  2019-09-30       Impact factor: 4.036
  7 in total

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