Alkyl nitrite-enabled palladium-catalyzed terminal selective oxidative cyclization of 4-penten-1-ols.

Oxidative cyclization of 4-penten-1-ols using a Pd catalyst and -BuONO or -BuONO/-benzoquinone afforded 3-hydroxy- and 3-methoxytetrahydropyrans terminal selective nucleophilic attack. The radicals formed from -BuONO and O operate as critical oxidants and ligands for Pd.