Literature DB >> 20450157

Copper-mediated aerobic oxidative trifluoromethylation of terminal alkynes with Me3SiCF3.

Lingling Chu1, Feng-Ling Qing.   

Abstract

An efficient copper-mediated trifluoromethylation of terminal alkynes with nucleophilic trifluoromethylating reagent (Me(3)SiCF(3)) was developed. Both aromatic alkynes and aliphatic alkynes were effective, and a variety of functionalities such as amino, -OMe, -CO(2)Et, -Br, and -NO(2) were tolerated under the reaction conditions. This reaction provides a general, straightforward, and practically useful method to prepare trifluoromethylated acetylenes.

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Year:  2010        PMID: 20450157     DOI: 10.1021/ja102175w

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


  9 in total

Review 1.  Aerobic copper-catalyzed organic reactions.

Authors:  Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal:  Chem Rev       Date:  2013-06-20       Impact factor: 60.622

2.  Room temperature aryl trifluoromethylation via copper-mediated oxidative cross-coupling.

Authors:  Todd D Senecal; Andrew T Parsons; Stephen L Buchwald
Journal:  J Org Chem       Date:  2011-01-14       Impact factor: 4.354

3.  Iron(II)-catalyzed trifluoromethylation of potassium vinyltrifluoroborates.

Authors:  Andrew T Parsons; Todd D Senecal; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-10       Impact factor: 15.336

4.  Efficient Synthesis of β-CF3/SCF3-Substituted Carbonyls via Copper-Catalyzed Electrophilic Ring-Opening Cross-Coupling of Cyclopropanols.

Authors:  Yong Li; Zhishi Ye; Tabitha M Bellman; Teng Chi; Mingji Dai
Journal:  Org Lett       Date:  2015-04-17       Impact factor: 6.072

Review 5.  Progress in copper-catalyzed trifluoromethylation.

Authors:  Guan-Bao Li; Chao Zhang; Chun Song; Yu-Dao Ma
Journal:  Beilstein J Org Chem       Date:  2018-01-17       Impact factor: 2.883

6.  Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation.

Authors:  Xiaoqiang Huang; Xinyao Li; Ning Jiao
Journal:  Chem Sci       Date:  2015-07-20       Impact factor: 9.825

Review 7.  Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

Authors:  Xiaowei Li; Xiaolin Shi; Xiangqian Li; Dayong Shi
Journal:  Beilstein J Org Chem       Date:  2019-09-23       Impact factor: 2.883

8.  Cu-Mediated trifluoromethylation of benzyl, allyl and propargyl methanesulfonates with TMSCF3.

Authors:  Xueliang Jiang; Feng-Ling Qing
Journal:  Beilstein J Org Chem       Date:  2013-12-12       Impact factor: 2.883

Review 9.  Pauson-Khand reaction of fluorinated compounds.

Authors:  Jorge Escorihuela; Daniel M Sedgwick; Alberto Llobat; Mercedes Medio-Simón; Pablo Barrio; Santos Fustero
Journal:  Beilstein J Org Chem       Date:  2020-07-14       Impact factor: 2.883

  9 in total

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