Studies On C-O Bond Formations Using NHPI And TEMPO⁺BF₄^-

This thesis makes a description of N-hydroxyphthalimide (NHPI) and2,2,6,6-tetramethylpiperidinium-1-oxo trafluoroborate (TEMPO+BF4-) involved carbon-oxygen bond formation via intermolecular radical cross-coupling and intramolecular cyclization, respectively. It consists of three chapters:In the first chapter, the physical property and chemical reactivity of nitroxides are briefly reviewed firstly. Then various NHPI and TEMPO+involved reactions of the C-O single bond and C=O double bond formation and its application in the synthesis of natural products are elaborated.In the second chapter, we report an efficient esterification of aldehydes with NHPI to form C-O bond via a radical cross-coupling process using PhI(OAc)2or air as the oxidants.In the third chapter, an efficient and synthetically useful intramolecular cyclization of2-hydroaromatic ketones via C-O bond formation to synthesis of2-hydrobenzofuran-3-one using TEMPO+BF4-as the oxidant was successively developed.