title: Direct Conversion of Haloarenes to Phenols under Mild, Transition-Metal-Free Conditions.
abstract: A high-yielding and practical method for the synthesis of phenols from electron-deficient haloarenes and heteroarenes has been developed. The products are formed from acetohydroxamic acid as the hydroxide source via a novel SNAr reaction/Lossen rearrangement sequence. Notably, these reactions employ inexpensive and air-stable reagents, require no special handling, occur under mildly basic conditions, and form products in high yields in the presence of electrophilic and protic functionality. The utility of this methodology is demonstrated by the high-yielding hydroxylation of two base-sensitive complex substrates.
authors.affiliation: Department of Process & Analytical Chemistry, Merck Research Laboratories , 126 East Lincoln Avenue, Rahway, New Jersey 07065, United States.
authors.forename: Patrick S
authors.initials: PS
authors.lastname: Fier
authors.affiliation: Department of Process & Analytical Chemistry, Merck Research Laboratories , 126 East Lincoln Avenue, Rahway, New Jersey 07065, United States.
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Maloney