Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts : New Entries to Aromatic Amides

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http://hdl.handle.net/10138/331474

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Mkrtchyan , S , Jakubczyk , M , Lanka , S , Pittelkow , M & Iaroshenko , V O 2021 , ' Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts : New Entries to Aromatic Amides ' , Molecules , vol. 26 , no. 10 , 2957 . https://doi.org/10.3390/molecules26102957

Title: Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts : New Entries to Aromatic Amides
Author: Mkrtchyan, Satenik; Jakubczyk, Michal; Lanka, Suneel; Pittelkow, Michael; Iaroshenko, Viktor O.
Other contributor: University of Helsinki, Helsinki Institute of Sustainability Science (HELSUS)

Date: 2021-05-16
Language: eng
Number of pages: 27
Belongs to series: Molecules
ISSN: 1420-3049
DOI: https://doi.org/10.3390/molecules26102957
URI: http://hdl.handle.net/10138/331474
Abstract: We describe a mechanism-guided discovery of a synthetic methodology that enables the preparation of aromatic amides from 2-bromo-2,2-difluoroacetamides utilizing a copper-catalyzed direct arylation. Readily available and structurally simple aryl precursors such as aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts were used as the source for the aryl substituents. The scope of the reactions was tested, and the reactions were insensitive to the electronic nature of the aryl groups, as both electron-rich and electron-deficient aryls were successfully introduced. A wide range of 2-bromo-2,2-difluoroacetamides as either aliphatic or aromatic secondary or tertiary amides were also reactive under the developed conditions. The described synthetic protocols displayed excellent efficiency and were successfully utilized for the expeditious preparation of diverse aromatic amides in good-to-excellent yields. The reactions were scaled up to gram quantities.
Subject: fluorine
amides
copper
catalysis
C-C-coupling
boronic acids
aryl trialkoxysilanes
dimethyl-aryl-sulfonium salts
PHOTOREDOX CATALYSIS
ARYLBORONATE ESTERS
CROSS-COUPLINGS
BOND FORMATION
AMINODIFLUOROALKYLATION
TRANSFORMATION
RECOGNITION
MECHANISM
ACCESS
116 Chemical sciences
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