title: A Family of Routes to Substituted Phenols, Including Meta-Substituted Phenols.
abstract: A new family of routes to substituted phenols has been developed. 2-Bromo-3-methoxycyclohex-2-en-1-ones are readily deprotonated at C-6, and the resulting anions react smoothly with a variety of electrophiles; treatment with DBU in PhMe at room temperature then results in efficient aromatization to benzene derivatives of a regiochemically defined substitution pattern. This sequence affords phenolic azides (ArN3), sulfides (ArSR, ArSAr'), selenides (ArSePh), alcohols [ArCH(OH)R], amino derivatives [ArCH(NHSO2Ar')R), and 1,2-benzenediols. A complementary set of substitution patterns is obtained by DIBAL-H reduction or reaction with a Grignard reagent before aromatization; the latter process gives compounds in which the newly introduced substituent is meta to the phenolic hydroxyl.
authors.affiliation: Chemistry Department, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Wenjie
authors.initials: W
authors.lastname: Shao
authors.affiliation: Chemistry Department, University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Derrick L J
authors.initials: DL
authors.lastname: Clive