Literature DB >> 22612441

Electrophilic trifluoromethylation by copper-catalyzed addition of CF3-transfer reagents to alkenes and alkynes.

Pär G Janson1, Ibrahim Ghoneim, Nadia O Ilchenko, Kálmán J Szabó.   

Abstract

Regio- and stereoselective Cu-catalyzed addition of the above hypervalent iodine reagent to alkynes and alkenes was achieved. In the presence of CuI, the reaction is suitable to perform trifluoromethyl-benzoyloxylation and trifluoromethyl-halogenation of alkenes and alkynes. Electron-donating substituents accelerate the process, and alkenes react faster than alkynes emphasizing the electrophilic character of the addition reaction.

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Year:  2012        PMID: 22612441     DOI: 10.1021/ol3011419

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


  23 in total

1.  Copper-catalyzed oxytrifluoromethylation of unactivated alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

2.  Enantioselective functionalization of radical intermediates in redox catalysis: copper-catalyzed asymmetric oxytrifluoromethylation of alkenes.

Authors:  Rong Zhu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-16       Impact factor: 15.336

3.  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

4.  Mild silver-mediated geminal difluorination of styrenes using an air- and moisture-stable fluoroiodane reagent.

Authors:  Nadia O Ilchenko; Boris O A Tasch; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-21       Impact factor: 15.336

5.  Catalytic Intramolecular Aminofluorination, Oxyfluorination, and Carbofluorination with a Stable and Versatile Hypervalent Fluoroiodine Reagent.

Authors:  Weiming Yuan; Kálmán J Szabó
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-09       Impact factor: 15.336

Review 6.  Addition of CF3 across unsaturated moieties: a powerful functionalization tool.

Authors:  Estíbaliz Merino; Cristina Nevado
Journal:  Chem Soc Rev       Date:  2014-05-02       Impact factor: 54.564

7.  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

8.  Cation versus Radical: Studies on the C/O Regioselectivity in Electrophilic Tri-, Di- and Monofluoromethylations of β-Ketoesters.

Authors:  Yu-Dong Yang; Xu Lu; Guokai Liu; Etsuko Tokunaga; Seiji Tsuzuki; Norio Shibata
Journal:  ChemistryOpen       Date:  2012-10-11       Impact factor: 2.911

9.  Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent.

Authors:  Xiao-Ping Wang; Jin-Hong Lin; Cheng-Pan Zhang; Ji-Chang Xiao; Xing Zheng
Journal:  Beilstein J Org Chem       Date:  2013-11-25       Impact factor: 2.883

10.  Direct C-H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis.

Authors:  Ren Tomita; Yusuke Yasu; Takashi Koike; Munetaka Akita
Journal:  Beilstein J Org Chem       Date:  2014-05-12       Impact factor: 2.883

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