Literature DB >> 27214849

Trifluoromethylation of Arylsilanes with [(phen)CuCF3 ].

Johannes Morstein1, Haiyun Hou1, Chen Cheng1, John F Hartwig2.   

Abstract

A method for the trifluoromethylation of arylsilanes is reported. The reaction proceeds with [(phen)CuCF3 ] as the CF3  source under mild, oxidative conditions with high functional-group compatibility. This transformation complements prior trifluoromethylation of arenes in several ways. Most important, this method converts arylsilanes formed by the silylation of aryl C-H bonds to trifluoromethylarenes, thereby allowing the conversion of arenes to trifluoromethylarenes. The unique capabilities of the reported method are demonstrated by the conversion of a C-H bond into a C-CF3 bond in active pharmaceutical ingredients which do not undergo this overall transformation by alternative functionalization processes, including a combination of borylation and trifluoromethylation.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  arenes; copper; cross-coupling; fluorine; silanes

Mesh:

Substances:

Year:  2016        PMID: 27214849      PMCID: PMC4976628          DOI: 10.1002/anie.201601163

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  22 in total

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Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation.

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3.  Iridium-catalyzed C-H borylation of pyridines.

Authors:  Scott A Sadler; Hazmi Tajuddin; Ibraheem A I Mkhalid; Andrei S Batsanov; David Albesa-Jove; Man Sing Cheung; Aoife C Maxwell; Lena Shukla; Bryan Roberts; David C Blakemore; Zhenyang Lin; Todd B Marder; Patrick G Steel
Journal:  Org Biomol Chem       Date:  2014-10-07       Impact factor: 3.876

4.  Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate.

Authors:  Tatsuo Ishiyama; Jun Takagi; Kousaku Ishida; Norio Miyaura; Natia R Anastasi; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-01-23       Impact factor: 15.419

5.  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

6.  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

7.  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

8.  New Electrophilic Trifluoromethylating Agents.

Authors:  Jing-Jing Yang; Robert L. Kirchmeier; Jean'ne M. Shreeve
Journal:  J Org Chem       Date:  1998-04-17       Impact factor: 4.354

9.  Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol.

Authors:  Chen Cheng; John F Hartwig
Journal:  Science       Date:  2014-02-21       Impact factor: 47.728

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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  9 in total

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Authors:  Ruth Dorel; Philip Boehm; Daniel P Schwinger; John F Hartwig
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2.  Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis.

Authors:  Caleb Karmel; Zhewei Chen; John F Hartwig
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3.  Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale.

Authors:  Joel W Beatty; James J Douglas; Richard Miller; Rory C McAtee; Kevin P Cole; Corey R J Stephenson
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4.  Copper-Mediated C-N Coupling of Arylsilanes with Nitrogen Nucleophiles.

Authors:  Johannes Morstein; Eric D Kalkman; Christian Bold; Chen Cheng; John F Hartwig
Journal:  Org Lett       Date:  2016-09-30       Impact factor: 6.005

5.  Correction to "Copper-Mediated C-N Coupling of Arylsilanes with Nitrogen Nucleophiles".

Authors:  Johannes Morstein; Eric D Kalkman; Christian Bold; Chen Cheng; John F Hartwig
Journal:  Org Lett       Date:  2016-11-11       Impact factor: 6.072

Review 6.  Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F).

Authors:  Louise Ruyet; Tatiana Besset
Journal:  Beilstein J Org Chem       Date:  2020-05-18       Impact factor: 2.883

7.  An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes.

Authors:  Vasiliy M Muzalevskiy; Zoia A Sizova; Vladimir T Abaev; Valentine G Nenajdenko
Journal:  Molecules       Date:  2021-12-04       Impact factor: 4.411

8.  The dioxasilepanyl group as a versatile organometallic unit: studies on stability, reactivity, and utility.

Authors:  Hayate Saito; Jun Shimokawa; Hideki Yorimitsu
Journal:  Chem Sci       Date:  2021-06-08       Impact factor: 9.825

9.  Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes.

Authors:  Samuel J Hein; Dan Lehnherr; William R Dichtel
Journal:  Chem Sci       Date:  2017-06-09       Impact factor: 9.825

  9 in total

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