Oxidative Dearomatization of Phenols and Related Substrates

Of particular use are the reactions of oxidative dearomatization of 4- or 2-substituted phenols 222 and 225 with -iodanes in the presence of an external or internal nucleophile (Nu) leading to the respective 

The oxidative spirocyclization of phenolic substrates containing an internal nitrogen nucleophile provides a useful tool for the construction of nitrogen heterocycles [287, 315-318], For example, the hypervalent iodine-induced cyclization of phenolic oxazolines 251 affords the synthetically useful spirolactam products 

This stereoselective process has been directly applied toward the formal synthesis of (-)-platensimycin, an important antibiotic agent [328]. 

Oxidative 1,2- and 1,3-alkyl shifts mediated by a hypervalent iodine reagent using simple and inexpensive phenol derivatives 267 enable rapid construction of highly functionalized scaffolds containing a prochiral 

Aniline derivatives can be oxidatively dearomatized analogously to the phenol derivatives. In particular, the oxidative //Ji o-tluorination of para-substituted tosylated anilines 286 using hypervalent iodine reagents 

---