Intramolecular Palladium-Catalyzed Ring Opening of Oxabenzonorbornadienes with C<sub>1</sub>-Tethered Aryl Halides
Samuel Koh, Austin Pounder, Elizabeth Brown, William Tam
Abstract
-tethered aryl halides was investigated using palladium catalysts to form fused tetracyclic frameworks. The reaction was generally found to synthesize 1,2-dihydronaphthalen-1-ol products with mild selectivity but was capable of synthesizing dehydrated naphthalene products in excellent yield and selectivity. Substituent effects on oxabenzonorbornadiene and on the iodoarene were explored along with the effects of varying tether length, where an efficient reaction was observed in nearly all cases. A total of 16 examples are reported with yields ranging from 0 to 96%.
Topics & Concepts
ChemistryIntramolecular forceArylPalladiumSubstituentSelectivityNaphthaleneCatalysisHalideRing (chemistry)Yield (engineering)Medicinal chemistryCombinatorial chemistryOrganic chemistryMetallurgyMaterials scienceAlkylCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsAxial and Atropisomeric Chirality Synthesis