Synthesis of Highly Substituted Adamantanones from Bicyclo[3.3.1]nonanes

Trifluoromethanesulfonic acid and other electrophiles promote formation of the adamantanone core from the readily accessible 1,5-dimethyl-3,7-dimethylenebicyclo[3.3.1]nonan-9-one 2. Because adamantyl cation 3 can be trapped by a range of nucleophiles, including aromatic and heteroaromatic rings, alcohol, nitriles, and halides, access to a wide variety of functionality at the newly formed tertiary position is provided

N -bromosuccinimide-induced aminocyclization-aziridine ring-expansion cascade: An asymmetric and highly stereoselective approach toward the synthesis of azepane

10.1021/ol5005609Organic Letters1682134-2137ORLE

Palladium(III)-Catalyzed Fluorination of Arylboronic Acid Derivatives

A practical, palladium-catalyzed synthesis of aryl fluorides from arylboronic acid derivatives is presented. The reaction is operationally simple and amenable to multigram-scale synthesis. Evaluation of the reaction mechanism suggests a single-electron-transfer pathway, involving a Pd(III) intermediate that has been isolated and characterized