Literature DB >> 27346239

Direct Access to α,α-Difluoroacylated Arenes by Palladium-Catalyzed Carbonylation of (Hetero)Aryl Boronic Acid Derivatives.

Thomas L Andersen1, Mette W Frederiksen1, Katrine Domino1, Troels Skrydstrup2.   

Abstract

A palladium-catalyzed carbonylative coupling of (hetero)aryl boronates or boronic acid salts with carbon monoxide and α-bromo-α,α-difluoroamides and bromo-α,α-difluoroesters is described herein. The method is useful for the synthesis of a diverse selection of (hetero)aryl α,α-difluoro-β-ketoamides and α,α-difluoro-β-ketoesters, which are useful building blocks for the generation of functionalized difluoroacylated and difluoroalkyl arenes. The method could be further extended to a one-pot protocol for the formation of difluoroacetophenones.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbonylation; cross-coupling; fluorine; palladium; synthetic methods

Year:  2016        PMID: 27346239     DOI: 10.1002/anie.201604152

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


  5 in total

1.  Metal-catalyzed Decarboxylative Fluoroalkylation Reactions.

Authors:  Brett R Ambler; Ming-Hsiu Yang; Ryan A Altman
Journal:  Synlett       Date:  2016-12       Impact factor: 2.454

Review 2.  The Fascinating Chemistry of α-Haloamides.

Authors:  Anna Fantinati; Vinicio Zanirato; Paolo Marchetti; Claudio Trapella
Journal:  ChemistryOpen       Date:  2020-01-13       Impact factor: 2.911

3.  Generation of formaldehyde and formaldehyde-d2 for hydroxymethylations and hydroxydeuteromethylations of difluoroenolates and difluorobenzyl carbanions.

Authors:  Hari R Khatri; Changho Han; Reem A Alkhodier; Amna T Adam; Baharul Islam; David A Colby
Journal:  Chem Commun (Camb)       Date:  2022-05-03       Impact factor: 6.065

Review 4.  Indolylboronic Acids: Preparation and Applications.

Authors:  Marek Čubiňák; Tereza Edlová; Peter Polák; Tomáš Tobrman
Journal:  Molecules       Date:  2019-09-28       Impact factor: 4.411

5.  Selective single C-F bond arylation of trifluoromethylalkene derivatives.

Authors:  Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

  5 in total

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