Divergent synthetic route to exo -methylene-type indanes and benzoxepines: dramatic effect of acid catalyst selection

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ID: 315066
2026
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Abstract
Abstract 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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Authors Hiroto Okawa, Masahiro Anada, Shunsuke Sueki, Kosho Makino, Tomoko Kawasaki‐Takasuka, Keiji Mori
Journal bulletin of the chemical society of japan
Year 2026
DOI
10.1093/bulcsj/uoag066
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