Oxetanes are frequently utilized in organic synthesis, both as target products and
as fairly reactive intermediates. Whereas ring cleavage of oxetanes through polar
mechanisms has been extensively investigated, their radical-based counterparts remain
underexplored. We used zirconocene and photoredox catalysis to open an oxetane ring
in a radical manner. In our protocol, the reaction selectively delivers the more-substituted
alcohols via putative less-stable radicals. This method not only affords the corresponding
hydrogenated products, but also provides unique benzylidene acetal products.
Key words
zirconocene - photoredox catalysis - oxetanes - reverse regioselectivity - C–O bond
homolysis - radicals