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Photoredox Catalytic Pentafluorosulfanylative Domino Cyclization of α-Substituted Alkenes to Oxaheterocycles by Using SF$_{6}$

Rombach, David; Birenheide, Bernhard; Wagenknecht, Hans-Achim 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)

Abstract:
Virtually inert sulfur hexafluoride becomes a precious pentafluorosulfanylation agent, if properly activated by photoredox catalysis, to access α-fluoro and α-alkoxy SF$_{5}$-compounds. This advanced protocol converts SF$_{6}$ in the presence of alkynols as bifunctional C−C- and C−O-bond forming reagents directly into pentafluorosulfanylated oxygen-containing heterocycles in a single step from α-substituted alkenes. The proposed mechanism is supported by theoretical calculations and gives insights not only in the pentafluorosulfanylation step but also into formation of the carbon-carbon bond and is in full agreement with Baldwin's cyclization rules. The key step is a radical type 5-, 6- respectively 7-exo-dig-cyclization. The synthesized oxaheterocycles cannot be simply prepared by other synthetic methods, show a high level of structural complexity and significantly expand the scope of pentafluorosulfanylated building blocks valuable for medicinal and material chemistry.


Verlagsausgabe §
DOI: 10.5445/IR/1000133588
Veröffentlicht am 03.06.2021
Originalveröffentlichung
DOI: 10.1002/chem.202100767
Scopus
Zitationen: 7
Dimensions
Zitationen: 12
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2021
Sprache Englisch
Identifikator ISSN: 0947-6539, 1521-3765
KITopen-ID: 1000133588
Erschienen in Chemistry - A European Journal
Verlag John Wiley and Sons
Band 27
Heft 31
Seiten 8088-8093
Nachgewiesen in Scopus
Web of Science
Dimensions
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