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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