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

Katrine Domino; Cedrick Veryser; Benjamin A. Wahlqvist; Cecilie Gaardbo; Karoline T. Neumann; Kim Daasbjerg; Wim M. DeBorggraeve; Troels Skrydstrup

doi:10.1002/anie.201802647

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

Katrine Domino, Cedrick Veryser, Benjamin A. Wahlqvist, Cecilie Gaardbo, Karoline T. Neumann, Kim Daasbjerg, Wim M. DeBorggraeve, Troels Skrydstrup^*

^*Corresponding author af dette arbejde

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

39 Citationer (Scopus)

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.

Originalsprog	Engelsk
Tidsskrift	Angewandte Chemie - International Edition
Vol/bind	57
Nummer	23
Sider (fra-til)	6858-6862
Antal sider	6
ISSN	1433-7851
DOI	https://doi.org/10.1002/anie.201802647
Status	Udgivet - 4 jun. 2018

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title = "Direct Access to Aryl Bis(trifluoromethyl)carbinols from Aryl Bromides or Fluorosulfates: Palladium-Catalyzed Carbonylation",

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.",

keywords = "Aryl halides, Carbonylation, Fluorine, Isotopic labeling, Palladium",

author = "Katrine Domino and Cedrick Veryser and Wahlqvist, {Benjamin A.} and Cecilie Gaardbo and Neumann, {Karoline T.} and Kim Daasbjerg and DeBorggraeve, {Wim M.} and Troels Skrydstrup",

year = "2018",

month = jun,

day = "4",

doi = "10.1002/anie.201802647",

language = "English",

volume = "57",

pages = "6858--6862",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

number = "23",

}

Direct Access to Aryl Bis(trifluoromethyl)carbinols from Aryl Bromides or Fluorosulfates: Palladium-Catalyzed Carbonylation. / Domino, Katrine; Veryser, Cedrick; Wahlqvist, Benjamin A. et al.
I: Angewandte Chemie - International Edition, Bind 57, Nr. 23, 04.06.2018, s. 6858-6862.

Publikation: Bidrag til tidsskrift/Konferencebidrag i tidsskrift /Bidrag til avis › Tidsskriftartikel › Forskning › peer review

TY - JOUR

T1 - Direct Access to Aryl Bis(trifluoromethyl)carbinols from Aryl Bromides or Fluorosulfates

T2 - Palladium-Catalyzed Carbonylation

AU - Domino, Katrine

AU - Veryser, Cedrick

AU - Wahlqvist, Benjamin A.

AU - Gaardbo, Cecilie

AU - Neumann, Karoline T.

AU - Daasbjerg, Kim

AU - DeBorggraeve, Wim M.

AU - Skrydstrup, Troels

PY - 2018/6/4

Y1 - 2018/6/4

N2 - 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.

AB - 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.

KW - Aryl halides

KW - Carbonylation

KW - Fluorine

KW - Isotopic labeling

KW - Palladium

UR - http://www.scopus.com/inward/record.url?scp=85046364091&partnerID=8YFLogxK

U2 - 10.1002/anie.201802647

DO - 10.1002/anie.201802647

M3 - Journal article

C2 - 29663685

AN - SCOPUS:85046364091

SN - 1433-7851

VL - 57

SP - 6858

EP - 6862

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 23

ER -

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

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