Literature DB >> 29663685

Direct Access to Aryl Bis(trifluoromethyl)carbinols from Aryl Bromides or Fluorosulfates: Palladium-Catalyzed Carbonylation.

Katrine Domino1, Cedrick Veryser1,2, Benjamin A Wahlqvist1, Cecilie Gaardbo1, Karoline T Neumann1, Kim Daasbjerg1, Wim M De Borggraeve2, Troels Skrydstrup1.   

Abstract

A palladium-catalyzed carbonylative approach for the direct conversion of (hetero)aryl bromides into their α,α-bis(trifluoromethyl)carbinols is described, and it employs only stoichiometric amounts of carbon monoxide and trifluoromethyltrimethylsilane. In addition, aryl fluorosulfates proved highly compatible with these reaction conditions. The method is tolerant of a diverse set of functional groups, and it is adaptable to late-stage carbon-isotope labeling.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  aryl halides; carbonylation; fluorine; isotopic labeling; palladium

Year:  2018        PMID: 29663685     DOI: 10.1002/anie.201802647

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


  2 in total

1.  Site-Selective, Modular Diversification of Polyhalogenated Aryl Fluorosulfates (ArOSO2 F) Enabled by an Air-Stable PdI Dimer.

Authors:  Marvin Mendel; Indrek Kalvet; Daniel Hupperich; Guillaume Magnin; Franziska Schoenebeck
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-16       Impact factor: 15.336

2.  Rapid and column-free syntheses of acyl fluorides and peptides using ex situ generated thionyl fluoride.

Authors:  Cayo Lee; Brodie J Thomson; Glenn M Sammis
Journal:  Chem Sci       Date:  2021-11-29       Impact factor: 9.825

  2 in total

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