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An Intramolecular Iodine‐Catalyzed C(sp 3 )−H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans
Author(s) -
Koch Vanessa,
Bräse Stefan
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100652
Subject(s) - chemistry , intramolecular force , tetrahydrofuran , catalysis , reagent , iodine , photochemistry , redox , combinatorial chemistry , transition metal , oxygen , carbon fibers , catalytic cycle , inorganic chemistry , organic chemistry , solvent , composite number , composite material , materials science
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.