Metastable Intermediates (Isoindenes, Isofluorenes, and Isobenzofurans) from Alkyne Precursors via Free Carbenes
Abstract
We report here reactions between a free carbene center and a suitably appended π-bond (C═X) that give rise to reactive intermediates that, in turn, undergo various types of additional transformations (cycloadditions, rearrangements, and ring openings). Participation of the following C═X functional groups is demonstrated: alkene, arene, heteroarene, aldehyde, ester, ketone, amide, and carbamate. The overall transformations are thermally driven and often produce no byproducts. Each is initiated by the generation of a carbene that is fueled by the potential energy provided by two complementary alkyne coreactants.
Fields of Study & Subjects
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Cyclopropane Reaction Mechanisms
Chemical Reactions and Mechanisms
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 9
- Pages
- 2929–2934
- Publication date
- 23 February 2026
- Language
- EN