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 for this work

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

38 Citations (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.

Original language	English
Journal	Angewandte Chemie - International Edition
Volume	57
Issue	23
Pages (from-to)	6858-6862
Number of pages	6
ISSN	1433-7851
DOIs	https://doi.org/10.1002/anie.201802647
Publication status	Published - 19 Jun 2018

Keywords

Aryl halides
Carbonylation
Fluorine
Isotopic labeling
Palladium

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10.1002/anie.201802647

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@article{16ea336eea874fe9abbabd220877c2a7,

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 = "19",

doi = "10.1002/anie.201802647",

language = "English",

volume = "57",

pages = "6858--6862",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

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.
In: Angewandte Chemie - International Edition, Vol. 57, No. 23, 19.06.2018, p. 6858-6862.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › 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 - 2018/6/19

Y1 - 2018/6/19

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

Abstract

Keywords

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