Synthesis of Dibenzotropones by Alkyne-Carbonyl Metathesis
Maryam Sobhani, Anna Frey, Andre Rettmann, Richard Thom, Alexander Villinger, Peter Ehlers, Peter Langer
Abstract
Dibenzocycloheptanones (dibenzotropones) were prepared by Brønsted acid mediated intramolecular alkyne-carbonyl metathesis (ACM) reactions. The cyclization precursors are readily available by Sonogashira reaction of 2-bromobenzoyl chloride with terminal alkynes, followed by Suzuki reactions with benzaldehydes. The ACM reactions are highly modular and atom economic and allow for the construction of two regioisomeric series of dibenzotropones.
Topics & Concepts
ChemistryAlkyneSonogashira couplingMetathesisOxalyl chlorideIntramolecular reactionChlorideIntramolecular forceCombinatorial chemistryOrganic chemistryMedicinal chemistryCatalysisPalladiumPolymerPolymerizationSynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisCyclopropane Reaction Mechanisms