Reactions of Electrophilic Allenoates [and Isocyanates/Isothiocyanates] with a 2-Alkynylpyridine via a Free Carbene Intermediate
A pyridine containing a 2-alkynyl substituent armed with a carbene reporter group [R<sup>1</sup> = C(Me)<sub>2</sub>OAc] is shown to engage electrophilic allenes to generate intermediate free carbenes. Depending on the electron density at the carbene carbon atom, a feature that is modulated by the substituents on the allene substrate, the carbene will either rearrange or eject an acetate leaving group, leading to various types of indolizine-containing products. Iso(thio)cyanates react in an analogous fashion.
Authors
- Thomas R. Hoye (ORCID: https://orcid.org/0000-0001-9318-1477)
- Qian Xu (ORCID: https://orcid.org/0000-0002-8655-8683)
- Ruiqin Wang (ORCID: https://orcid.org/0000-0003-0049-885X)
Institutions
- University of Minnesota (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-10
- DOI
- https://doi.org/10.1021/acs.orglett.4c02387
- Citations
- 7
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- National Institute of General Medical Sciences