Experimental and Computational Investigation into the Formation, Rearrangements, and Capture of Carbonyl-Substituted Bicyclobutonium and Related Cations
Abstract We report the combined experimental and computational investigation of systems involving carbonyl-containing bicyclobutonium cation intermediates generated by I(III)-mediated oxidative Umpolung or acylation of cyclobutenes. The regio- and diastereoselectivity of their nucleophilic capture relies on the in situ formation of “locked” oxocarbenium intermediates and “unlocked” cyclobutyl cations.
Authors
- Pier Alexandre Champagne (ORCID: https://orcid.org/0000-0002-0546-7537)
- Yi Xiao (ORCID: https://orcid.org/0009-0008-6353-118X)
- Daniel Kaiser (ORCID: https://orcid.org/0000-0001-8895-9969)
- Philipp Spieß (ORCID: https://orcid.org/0000-0003-2674-0165)
- Teresa Antón‐Cánovas (ORCID: https://orcid.org/0000-0001-9454-9296)
- Zhi‐Jie Niu
- Nuno Maulide (ORCID: https://orcid.org/0000-0003-3643-0718)
- Aymen Benchouche (ORCID: https://orcid.org/0009-0007-9643-8902)
Institutions
- New Jersey Institute of Technology (US)
- University of Vienna (AT)
- CeMM Research Center for Molecular Medicine (AT)
Publication Details
- Journal
- JACS Au
- Published
- 2026-10-14
- DOI
- https://doi.org/10.1021/jacsau.6c01309
- Primary Topic
- Organic Chemistry Synthesis Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Austrian Science Fund
- American Chemical Society Petroleum Research Fund
- European Research Council