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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dc.contributor.author Mkrtchyan, Satenik
dc.contributor.author Jakubczyk, Michal
dc.contributor.author Lanka, Suneel
dc.contributor.author Pittelkow, Michael
dc.contributor.author Iaroshenko, Viktor O.
dc.date.accessioned 2021-06-17T07:51:01Z
dc.date.available 2021-06-17T07:51:01Z
dc.date.issued 2021-05-16
dc.identifier.citation 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
dc.identifier.other PURE: 165247433
dc.identifier.other PURE UUID: 77064d49-cde8-4d5d-a2b1-9b10b349e570
dc.identifier.other WOS: 000655048400001
dc.identifier.other ORCID: /0000-0002-5647-5326/work/95673805
dc.identifier.uri http://hdl.handle.net/10138/331474
dc.description.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. en
dc.format.extent 27
dc.language.iso eng
dc.relation.ispartof Molecules
dc.rights cc_by
dc.rights.uri info:eu-repo/semantics/openAccess
dc.subject fluorine
dc.subject amides
dc.subject copper
dc.subject catalysis
dc.subject C-C-coupling
dc.subject boronic acids
dc.subject aryl trialkoxysilanes
dc.subject dimethyl-aryl-sulfonium salts
dc.subject PHOTOREDOX CATALYSIS
dc.subject ARYLBORONATE ESTERS
dc.subject CROSS-COUPLINGS
dc.subject BOND FORMATION
dc.subject AMINODIFLUOROALKYLATION
dc.subject TRANSFORMATION
dc.subject RECOGNITION
dc.subject MECHANISM
dc.subject ACCESS
dc.subject 116 Chemical sciences
dc.title Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts : New Entries to Aromatic Amides en
dc.type Article
dc.contributor.organization Helsinki Institute of Sustainability Science (HELSUS)
dc.contributor.organization Department of Chemistry
dc.description.reviewstatus Peer reviewed
dc.relation.doi https://doi.org/10.3390/molecules26102957
dc.relation.issn 1420-3049
dc.rights.accesslevel openAccess
dc.type.version publishedVersion

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