Literature DB >> 21274956

Copper-catalyzed trifluoromethylation of aryl iodides with potassium (trifluoromethyl)trimethoxyborate.

Thomas Knauber1, Fatih Arikan, Gerd-Volker Röschenthaler, Lukas J Goossen.   

Abstract

Potassium (trifluoromethyl)trimethoxyborate is introduced as a new source of CF(3) nucleophiles in copper-catalyzed trifluoromethylation reactions. The crystalline salt is stable on storage, easy to handle, and can be obtained in near-quantitative yields simply by mixing B(OMe)(3), CF(3)SiMe(3), and KF. The trifluoromethylation reagent allows the conversion of various aryl iodides into the corresponding benzotrifluorides in high yields under mild, base-free conditions in the presence of catalytic quantities of a Cu(I)/1,10-phenanthroline complex.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Year:  2011        PMID: 21274956     DOI: 10.1002/chem.201002749

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  21 in total

1.  Silver-mediated trifluoromethylation of arenes using TMSCF3.

Authors:  Yingda Ye; Shin Hee Lee; Melanie S Sanford
Journal:  Org Lett       Date:  2011-09-20       Impact factor: 6.005

2.  Mechanistic and computational studies of oxidatively-induced aryl-CF3 bond-formation at Pd: rational design of room temperature aryl trifluoromethylation.

Authors:  Nicholas D Ball; J Brannon Gary; Yingda Ye; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

3.  Merging visible-light photocatalysis and transition-metal catalysis in the copper-catalyzed trifluoromethylation of boronic acids with CF3I.

Authors:  Yingda Ye; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2012-05-24       Impact factor: 15.419

4.  Expanding the scope of replicable unnatural DNA: stepwise optimization of a predominantly hydrophobic base pair.

Authors:  Thomas Lavergne; Mélissa Degardin; Denis A Malyshev; Henry T Quach; Kirandeep Dhami; Phillip Ordoukhanian; Floyd E Romesberg
Journal:  J Am Chem Soc       Date:  2013-04-02       Impact factor: 15.419

5.  Metallaphotoredox Perfluoroalkylation of Organobromides.

Authors:  Xiangbo Zhao; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2020-11-09       Impact factor: 15.419

Review 6.  Catalysis for fluorination and trifluoromethylation.

Authors:  Takeru Furuya; Adam S Kamlet; Tobias Ritter
Journal:  Nature       Date:  2011-05-26       Impact factor: 49.962

7.  A broadly applicable copper reagent for trifluoromethylations and perfluoroalkylations of aryl iodides and bromides.

Authors:  Hiroyuki Morimoto; Tetsu Tsubogo; Nichole D Litvinas; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-25       Impact factor: 15.336

8.  The palladium-catalyzed trifluoromethylation of vinyl sulfonates.

Authors:  Eun Jin Cho; Stephen L Buchwald
Journal:  Org Lett       Date:  2011-11-23       Impact factor: 6.005

9.  Copper-catalyzed trifluoromethylation of unactivated olefins.

Authors:  Andrew T Parsons; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2011-08-25       Impact factor: 15.336

10.  Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes.

Authors:  Brett R Ambler; Santosh Peddi; Ryan A Altman
Journal:  Org Lett       Date:  2015-04-24       Impact factor: 6.005

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