Work

Reactions of Electrophilic Allenoates [and Isocyanates/Isothiocyanates] with a 2-Alkynylpyridine via a Free Carbene Intermediate

Year: 2024

Type: article

Abstract: A pyridine containing a 2-alkynyl substituent armed with a carbene reporter group [R 1 = C(Me) 2 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c02387

Authors: Ruiqin Wang, Qian Xu, Thomas R. Hoye

Institution: University of Minnesota

Language: English

Topic: Chemical Reactions and Mechanisms

Subfield: Physical and Theoretical Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Cancer Institute, National Institute of General Medical Sciences

Awards: G1345980661, G506717095, Upgrade of a 500 MHz NMR Spectrometer for Applications in Biomedical Research, Cancer Center Support Grant