Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers

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Jakubczyk , M , Mkrtchyan , S , Shkoor , M , Lanka , S , Budzak , S , Ilias , M , Skorsepa , M & Iaroshenko , V O 2022 , ' Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers ' , Journal of the American Chemical Society , vol. 144 , no. 23 , pp. 10438-10445 . https://doi.org/10.1021/jacs.2c02611

Title: Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers
Author: Jakubczyk, Michal; Mkrtchyan, Satenik; Shkoor, Mohanad; Lanka, Suneel; Budzak, Simon; Ilias, Miroslav; Skorsepa, Marek; Iaroshenko, Viktor O.
Contributor organization: Helsinki Institute of Sustainability Science (HELSUS)
Department of Chemistry
Date: 2022-06-15
Language: eng
Number of pages: 8
Belongs to series: Journal of the American Chemical Society
ISSN: 0002-7863
DOI: https://doi.org/10.1021/jacs.2c02611
URI: http://hdl.handle.net/10138/346546
Abstract: Increased 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 OCF3 functionality. 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.
Subject: OXIDATIVE DESULFURIZATION-FLUORINATION
CONVENIENT SYNTHESIS
SUBSTITUTION
REACTIVITY
CHEMISTRY
FLUORIDE
DESIGN
SALTS
PAIRS
116 Chemical sciences
Peer reviewed: Yes
Rights: cc_by
Usage restriction: openAccess
Self-archived version: publishedVersion


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