The Ylide Dance: Base-Induced Furan Synthesis via Formal [3+2] Annulation of Phenacyl- and Alkenyl Sulfonium Salts
A methodology for the synthesis of substituted furans via an "ylide dance" sequence has been developed. The reaction involves phenacyl sulfonium salts and alkenyl- or propargyl sulfonium salts under basic conditions. The key feature is a stepwise evolution where a primary sulfur ylide, generated from phenacyl sulfonium salt and base, transforms into another ylide, which then undergoes conversion into yet another, a "third generation" ylide, culminating in the formation of the target furan.
Authors
- Beauty K. Chabuka (ORCID: https://orcid.org/0000-0001-5332-2415)
- Danil A. Myasnikov (ORCID: https://orcid.org/0000-0001-8889-9580)
- Igor V. Alabugin (ORCID: https://orcid.org/0000-0001-9289-3819)
- Igor V. Trushkov (ORCID: https://orcid.org/0000-0002-1614-416X)
- Maxim G. Uchuskin (ORCID: https://orcid.org/0000-0001-9008-7610)
- Elena Y. Mendogralo (ORCID: https://orcid.org/0000-0003-3721-8516)
- Anastasia Y. Khodus
Institutions
- Florida State University (US)
- Perm State University (RU)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c04395
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00