DFT Insights into the Mechanistic Switch from Carbene to Carbocation in B(C <sub>6</sub> F <sub>5</sub> ) <sub>3</sub> -Catalyzed Coupling of Diazooxindoles and Difluoroenoxysilanes in HFIP
This study provides theoretical evidence highlighting the pivotal role of HFIP in inducing a mechanistic shift from a carbene to a carbocation intermediate in the B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed coupling of diazooxindoles and difluoroenoxysilanes. Our computational results reveal a novel and unconventional reaction pathway, where a carbocation intermediate is formed, rather than the traditionally expected carbene intermediate.
Authors
- Ran Fang (ORCID: https://orcid.org/0000-0001-6804-6572)
- Canjie Xin
- Lizi Yang (ORCID: https://orcid.org/0000-0002-2855-0149)
Institutions
- China National Chemical Engineering (China) (CN)
- Shaanxi University of Science and Technology (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-10-13
- DOI
- https://doi.org/10.1021/acs.joc.5c01257
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00