Divergent synthetic route produces indanes and benzoxepines, highlighting acid catalyst importance.
A divergent synthetic route to indanes and benzoxepines is reported. The key to the divergence is the selection of the catalytic system. Whereas treating benzylidene malonate having a 1-alkoxyalkyl group at the ortho position with Sc(OTf)3 gave indanes via an internal redox reaction ([1,4]-hydride shift/cyclization), the simultaneous use of Sc(OTf)3 and PhCO2H afforded benzoxepines through an intramolecular nucleophilic substitution reaction.
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Okawa et al. (2026) studied this question.
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