A Family of Routes to Substituted Phenols, Including Meta-Substituted Phenols.
J Org Chem
; 80(24): 12280-7, 2015 Dec 18.
Article
em En
| MEDLINE
| ID: mdl-26589285
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.
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01-internacional
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MEDLINE
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article