Literature DB >> 31872488

Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

Ruth Dorel1, Philip Boehm1, Daniel P Schwinger1, John F Hartwig1.   

Abstract

A method for the nucleophilic fluorination of heptamethyl aryl trisiloxanes to form fluoroarenes is reported. The reaction proceeds in the presence of Cu(OTf)2 and KHF2 as the fluoride source under mild conditions for a broad range of heptamethyltrisiloxyarenes with high functional group tolerance. The combination of this method with the silylation of aryl C-H bonds enables the regioselective fluorination of non-activated arenes controlled by steric effects following a two-step protocol.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aryl silanes; copper; fluorination; fluoroarenes; nucleophilic fluoride

Year:  2020        PMID: 31872488      PMCID: PMC7266656          DOI: 10.1002/chem.201905040

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


  48 in total

Review 1.  Monofluorination of Organic Compounds: 10 Years of Innovation.

Authors:  Pier Alexandre Champagne; Justine Desroches; Jean-Denys Hamel; Mathilde Vandamme; Jean-François Paquin
Journal:  Chem Rev       Date:  2015-04-09       Impact factor: 60.622

2.  Palladium(II)-catalyzed selective monofluorination of benzoic acids using a practical auxiliary: a weak-coordination approach.

Authors:  Kelvin S L Chan; Masayuki Wasa; Xisheng Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-11       Impact factor: 15.336

3.  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
Journal:  J Am Chem Soc       Date:  2019-04-23       Impact factor: 15.419

Review 4.  Catalysis for fluorination and trifluoromethylation.

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

5.  Ortho-Functionalized Aryltetrazines by Direct Palladium-Catalyzed C-H Halogenation: Application to Fast Electrophilic Fluorination Reactions.

Authors:  Christelle Testa; Élodie Gigot; Semra Genc; Richard Decréau; Julien Roger; Jean-Cyrille Hierso
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-24       Impact factor: 15.336

6.  Nucleophilic aryl fluorination and aryl halide exchange mediated by a Cu(I)/Cu(III) catalytic cycle.

Authors:  Alicia Casitas; Mercè Canta; Miquel Solà; Miquel Costas; Xavi Ribas
Journal:  J Am Chem Soc       Date:  2011-11-14       Impact factor: 15.419

7.  Iridium-catalyzed silylation of aryl C-H bonds.

Authors:  Chen Cheng; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-01-06       Impact factor: 15.419

8.  Nickel-mediated oxidative fluorination for PET with aqueous [18F] fluoride.

Authors:  Eunsung Lee; Jacob M Hooker; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2012-10-12       Impact factor: 15.419

9.  Mild copper-mediated fluorination of aryl stannanes and aryl trifluoroborates.

Authors:  Yingda Ye; Melanie S Sanford
Journal:  J Am Chem Soc       Date:  2013-03-13       Impact factor: 15.419

10.  Regiospecific ortho-C-H Allylation of Benzoic Acids.

Authors:  A Stefania Trita; Agostino Biafora; Martin Pichette Drapeau; Philip Weber; Lukas J Gooßen
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-05       Impact factor: 15.336

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.