Divergent Approach to Highly Substituted Arenes via [3 + 3] Annulation of Vinyl Sulfoxonium Ylides with Ynones
Daksh Singh Davas, Dinesh Kumar Gopalakrishnan, Krishnendu Bar, Sandeep Kumar, Tarak Karmakar, Janakiram Vaitla
Abstract
Herein, we report the divergent benzannulation for highly substituted arenes using vinyl sulfoxonium ylides and ynones. The addition of ynone at the γ-position of vinyl sulfoxonium ylides leads to dienyl sulfoxonium ylide that can undergo selective annulation under different conditions to give m -terphenyls and parabens. Moreover, control experiments and quantum chemical calculations reveal two distinct reaction mechanisms for both annulations.
Topics & Concepts
AnnulationChemistryYlideOrganic chemistryCombinatorial chemistryQuantum chemicalMoleculeCatalysisCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions