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AuthorJakubczyk, Michał
AuthorMkrtchyan, Satenik
AuthorShkoor, Mohanad
AuthorLanka, Suneel
AuthorBudzák, Šimon
AuthorIliaš, Miroslav
AuthorSkoršepa, Marek
AuthorIaroshenko, Viktor O.
Available date2022-08-16T05:30:27Z
Publication Date2022-06-15
Publication NameJournal of the American Chemical Society
Identifierhttp://dx.doi.org/10.1021/jacs.2c02611
CitationJ. Am. Chem. Soc. 2022, 144, 23, 10438–10445
ISSN00027863
URIhttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85132016873&origin=inward
URIhttp://hdl.handle.net/10576/33094
AbstractIncreased interest in the trifluoromethoxy group in organic synthesis and medicinal chemistry has induced a demand for new, selective, general, and faster methods applicable to natural products and highly functionalized compounds at a later stage of hit-to-lead campaigns. Applying pyrylium tetrafluoroborate, we have developed a mechanochemical protocol to selectively substitute the aromatic amino group with the OCF3functionality. The scope of our method includes 31 examples of ring-substituted anilines, including amides and sulfonamides. Expected SNAr products were obtained in excellent yields. The presented concise method opens a pathway to new chemical spaces for the pharmaceutical industry.
SponsorThis research is supported by a grant from National Science Centre (NSC) Poland within the framework of the European Union’s Horizon 2020 research and innovation program under the Marie Skłodowska-Curie Grant 665778 (POLONEZ 2 Grant, no. 2016/21/P/ST5/00630). The computational part of this work was supported by the Slovak Research and Development Agency and the Scientific Grant Agency through VEGA 1/0562/20 and APVV-20-0098, respectively.
Languageen
PublisherAmerican Chemical Society
SubjectAromatic compounds
Cations
Reagents
Salts
Substitution reactions
TitleMechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers
TypeArticle
Pagination10438-10445
Issue Number23
Volume Number144
ESSN1520-5126


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