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An Intramolecular Iodine-Catalyzed C(sp$^{3}$)−H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans

Koch, Vanessa 1; Bräse, Stefan 1
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)


The first iodine-catalyzed cyclization reaction of aliphatic primary and secondary alcohols gives access to tetrahydrofurans through an intramolecular C(sp$^{3}$)−H activation. The reaction proceeds under mild reactions using either a floodlight lamp or daylight.
The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C−H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp$^{3}$)−H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.

Verlagsausgabe §
DOI: 10.5445/IR/1000136138
Veröffentlicht am 12.08.2021
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2021
Sprache Englisch
Identifikator ISSN: 1434-193X, 0075-4617, 0170-2041, 0365-5490, 0947-3440, 1099-0690, 1434-243X
KITopen-ID: 1000136138
Erschienen in European Journal of Organic Chemistry
Verlag John Wiley and Sons
Band 2021
Heft 24
Seiten 3478-3483
Vorab online veröffentlicht am 07.06.2021
Nachgewiesen in Web of Science
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