Year: 2026
Type: preprint
Abstract: We report a method to prepare alkenes through the base-promoted oxidative desaturation of alkylarenes and related weakly acidic functional groups. This process operates via a tandem deprotonative-halogenation and elimination sequence using haloarene halogen-transfer reagents. The use of potassium tert-butoxide with haloarene oxidants provides a simple means to desaturate a broad range of alkylarenes, acids, esters, and amides, as well as to aromatize saturated heterocycles. A critical feature for reaction success is the generation of tert-butanol from the tert-butoxide base which buffers the reaction solution to prevent anionic alkene polymerization. The utility of this approach is enhanced by its direct sequencing with additional base-promoted processes, such as hydrofunctionalization, to access formal homobenzylic C–H functionalization products.
Source: ChemRxiv
Institution: Colorado State University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7213942556