Divergent synthetic route to <i>exo</i> -methylene-type indanes and benzoxepines: dramatic effect of acid catalyst selection
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.
Authors
- Keiji Mori (ORCID: https://orcid.org/0000-0002-9878-993X)
- Masahiro Anada (ORCID: https://orcid.org/0000-0002-7691-5114)
- Tomoko Kawasaki‐Takasuka (ORCID: https://orcid.org/0000-0002-8468-7553)
- Hiroto Okawa
- Shunsuke Sueki (ORCID: https://orcid.org/0000-0003-0951-0018)
- Kosho Makino (ORCID: https://orcid.org/0000-0001-8635-6793)
Institutions
- Musashino University (JP)
- Tokyo University of Agriculture and Technology (JP)
Publication Details
- Journal
- Bulletin of the Chemical Society of Japan
- Published
- 2026-05-27
- DOI
- https://doi.org/10.1093/bulcsj/uoag066
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00