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Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ

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Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ. / Gedde, Oliver Raae; Jensen, Andreas Bonde; Golbækdal, Peter Illum et al.

In: Chemistry - A European Journal, Vol. 28, No. 34, e202200997, 06.2022.

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

Harvard

Gedde, OR, Jensen, AB, Golbækdal, PI & Skrydstrup, T 2022, 'Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ', Chemistry - A European Journal, vol. 28, no. 34, e202200997. https://doi.org/10.1002/chem.202200997

APA

Gedde, O. R., Jensen, A. B., Golbækdal, P. I., & Skrydstrup, T. (2022). Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ. Chemistry - A European Journal, 28(34), [e202200997]. https://doi.org/10.1002/chem.202200997

CBE

Gedde OR, Jensen AB, Golbækdal PI, Skrydstrup T. 2022. Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ. Chemistry - A European Journal. 28(34):Article e202200997. https://doi.org/10.1002/chem.202200997

MLA

Gedde, Oliver Raae et al. "Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ". Chemistry - A European Journal. 2022. 28(34). https://doi.org/10.1002/chem.202200997

Vancouver

Gedde OR, Jensen AB, Golbækdal PI, Skrydstrup T. Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ. Chemistry - A European Journal. 2022 Jun;28(34):e202200997. doi: 10.1002/chem.202200997

Author

Gedde, Oliver Raae ; Jensen, Andreas Bonde ; Golbækdal, Peter Illum et al. / Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ. In: Chemistry - A European Journal. 2022 ; Vol. 28, No. 34.

Bibtex

@article{cdf2959da96d47febaf6b38c17b3f6a1,
title = "Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ",
abstract = "An expedient ex-situ generation of difluoroiodomethane (DFIM) and its immediate use in a Pd-catalyzed difluoromethylation of aryl boronic acids and ester derivatives in a two-chamber reactor is reported. Heating a solution of bromodifluoroacetic acid with sodium iodide in sulfolane proved to be effective for the generation of near stoichiometric amounts of DFIM for the ensuing catalytic coupling step. A two-step difluoromethylation of aryl (pseudo)halides with tetrahydroxydiboron as a low-cost reducing agent, both promoted by Pd catalysis, proved effective to install this fluorine-containing C1 group onto several pharmaceutically relevant molecules. Finally, the method proved adaptable to deuterium incorporation by simply adding D2O to the DFIM-generating chamber.",
keywords = "aryl boronic acids, deuterium labeling, difluoroiodomethane, difluoromethylation, palladium catalysis",
author = "Gedde, {Oliver Raae} and Jensen, {Andreas Bonde} and Golb{\ae}kdal, {Peter Illum} and Troels Skrydstrup",
note = "{\textcopyright} 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.",
year = "2022",
month = jun,
doi = "10.1002/chem.202200997",
language = "English",
volume = "28",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "34",

}

RIS

TY - JOUR

T1 - Pd-Catalyzed Difluoromethylations of Aryl Boronic Acids, Halides, and Pseudohalides with ICF2H Generated ex Situ

AU - Gedde, Oliver Raae

AU - Jensen, Andreas Bonde

AU - Golbækdal, Peter Illum

AU - Skrydstrup, Troels

N1 - © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

PY - 2022/6

Y1 - 2022/6

N2 - An expedient ex-situ generation of difluoroiodomethane (DFIM) and its immediate use in a Pd-catalyzed difluoromethylation of aryl boronic acids and ester derivatives in a two-chamber reactor is reported. Heating a solution of bromodifluoroacetic acid with sodium iodide in sulfolane proved to be effective for the generation of near stoichiometric amounts of DFIM for the ensuing catalytic coupling step. A two-step difluoromethylation of aryl (pseudo)halides with tetrahydroxydiboron as a low-cost reducing agent, both promoted by Pd catalysis, proved effective to install this fluorine-containing C1 group onto several pharmaceutically relevant molecules. Finally, the method proved adaptable to deuterium incorporation by simply adding D2O to the DFIM-generating chamber.

AB - An expedient ex-situ generation of difluoroiodomethane (DFIM) and its immediate use in a Pd-catalyzed difluoromethylation of aryl boronic acids and ester derivatives in a two-chamber reactor is reported. Heating a solution of bromodifluoroacetic acid with sodium iodide in sulfolane proved to be effective for the generation of near stoichiometric amounts of DFIM for the ensuing catalytic coupling step. A two-step difluoromethylation of aryl (pseudo)halides with tetrahydroxydiboron as a low-cost reducing agent, both promoted by Pd catalysis, proved effective to install this fluorine-containing C1 group onto several pharmaceutically relevant molecules. Finally, the method proved adaptable to deuterium incorporation by simply adding D2O to the DFIM-generating chamber.

KW - aryl boronic acids

KW - deuterium labeling

KW - difluoroiodomethane

KW - difluoromethylation

KW - palladium catalysis

U2 - 10.1002/chem.202200997

DO - 10.1002/chem.202200997

M3 - Journal article

C2 - 35388933

VL - 28

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 34

M1 - e202200997

ER -