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AuthorMkrtchyan, Satenik
AuthorShkoor, Mohanad
AuthorPhanindrudu, Mandalaparthi
AuthorMedved′, Miroslav
AuthorSevastyanova, Olena
AuthorIaroshenko, Viktor O.
Available date2023-01-23T10:13:41Z
Publication Date2022-01-01
Publication NameJournal of Organic Chemistry
Identifierhttp://dx.doi.org/10.1021/acs.joc.2c02197
CitationJ. Org. Chem. 2023, 88, 2, 863–870 Publication Date:January 9, 2023 https://doi.org/10.1021/acs.joc.2c02197
ISSN00223263
URIhttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85146130268&origin=inward
URIhttp://hdl.handle.net/10576/38722
AbstractThe amide bond is prominent in natural and synthetic organic molecules endowed with activity in various fields. Among a wide array of amide synthetic methods, substitution on a pre-existing (O)C-N moiety is an underexplored strategy for the synthesis of amides. In this work, we disclose a new protocol for the defluorinative arylation of aliphatic and aromatic trifluoroacetamides yielding aromatic amides. The mechanochemically induced reaction of either arylboronic acids, trimethoxyphenylsilanes, diaryliodonium salts, or dimethyl(phenyl)sulfonium salts with trifluoroacetamides affords substituted aromatic amides in good to excellent yields. These nickel-catalyzed reactions are enabled by C-CF3 bond activation using Dy2O3 as an additive. The current protocol provides versatile and scalable routes for accessing a wide variety of substituted aromatic amides. Moreover, the protocol described in this work overcomes the drawbacks and limitations in the previously reported methods.
SponsorThis research project was supported by a grant (Nr. APVV-21-0362) from “Agentúra na podporu výskumu a vývoja” (The Slovak Research and Development Agency https://www.apvv.sk/). O.S. and V.I. are grateful to the Knut and Alice Wallenberg Foundation for financial support of their work through the Wallenberg Wood Science Center at KTH Royal Institute of Technology. M.M. acknowledges the support by the Operational Program Research, Development and Education─Project Nr. CZ.02.1.01/0.0/0.0/16_019/0000754 of the Ministry of Education, Youth and Sports of the Czech Republic.
Languageen
PublisherAmerican Chemical Society
SubjectMechanochemical
Aromatic Amides
Defluorinative Arylation
Trifluoroacetamides
TitleMechanochemical Defluorinative Arylation of Trifluoroacetamides: An Entry to Aromatic Amides
TypeArticle
Pagination863-870
Issue Number2
Volume Number88
ESSN1520-6904
dc.accessType Open Access


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