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Primary and Secondary Amines by Flavin-Photocatalyzed Consecutive Desulfonylation and Dealkylation of Sulfonamides
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SYSNO ASEP 0579795 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Primary and Secondary Amines by Flavin-Photocatalyzed Consecutive Desulfonylation and Dealkylation of Sulfonamides Author(s) Pavlovska, T. (CZ)
Weisheitelová, I. (CZ)
Pramthaisong, Chiranan (UOCHB-X)
Sikorski, M. (PL)
Jahn, Ullrich (UOCHB-X) ORCID
Cibulka, R. (CZ)Source Title Advanced Synthesis & Catalysis. - : Wiley - ISSN 1615-4150
Roč. 365, č. 24 (2023), s. 4662-4671Number of pages 10 s. Language eng - English Country DE - Germany Keywords consecutive catalysis ; oxidation ; photoredox catalysis ; protecting groups ; reduction ; sulfonamides OECD category Organic chemistry Method of publishing Open access Institutional support UOCHB-X - RVO:61388963 UT WOS 001102447100001 EID SCOPUS 85177467751 DOI 10.1002/adsc.202300843 Annotation Alkane-, arene-, and perfluoroalkanesulfonyl groups are widely used in organic synthesis to protect amino functionalities or to facilitate their installation. Protection of amino functions by a sulfonyl group to form sulfonamides is advantageous as they are easy to purify and tolerate various reaction conditions. On the other hand, sulfonyl group removal is difficult. Herein, we present a versatile metal-free photocatalytic reductive method for desulfonylation of sulfonamides and aryl sulfonates to the parent amines mediated by flavin derivatives, namely deazaisoalloxazines and deazaalloxazines, and visible light. Photocatalysis with 5-deazalloxazines is shown to even mediate the cleavage of perfluoroalkanesulfonamides (triflylamides and nonaflylamides), which is significantly more difficult than that of other sulfonamides and has previously not been achieved by photochemical means. The method is shown to perform consecutive desulfonylation and dealkylation of N-alkyl-N-phenylperfluoroalkanesulfonamides affording primary anilines. This occurs via consecutive reductive and oxidative catalytic cycles mediated by the flavin catalyst. The perfluoroalkylsulfonyl group fulfils a dual role serving as a protecting group and, after removal by the reductive cycle, as the species driving the oxidative dealkylation reaction. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2024 Electronic address https://doi.org/10.1002/adsc.202300843
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