title: A one-pot isomerization-arylation of 2,3-epoxycyclohexanone under controlled microwave heating.
abstract: A fast one-pot method has been developed for the direct preparation of 3-aryl-1,2-cyclohexanediones from 2,3-epoxycyclohexanone via a microwave-assisted tandem epoxy ketone isomerization-Heck arylation reaction. The preparative microwave-assisted reactions were performed preferentially in 50% aqueous poly(ethylene glycol) utilizing sodium acetate as the base. Within 5-30 min of directed microwave heating, employing less than 0.05 mol % of palladium acetate and no phosphine ligand, up to 72% yield of C3-arylated diketones was isolated in an overall environmentally benign process. On the basis of the chemical reactivity of proposed intermediates, a reaction pathway is proposed where the acetate base promotes the rearrangement of the 2,3-epoxycyclohexanone into the active mono-enol form of 1,2-cyclohexanedione. An alternative classically heated procedure for isomerization-C3-arylation of 2,3-epoxycyclohexanone in DMF is also reported.
authors.affiliation: Department of Medicinal Chemistry, Uppsala Biomedical Centre, Uppsala University, Box 574, SE-751 23 Uppsala, Sweden.
authors.forename: Andreas
authors.initials: A
authors.lastname: Svennebring
authors.forename: Neeraj
authors.initials: N
authors.lastname: Garg
authors.forename: Peter
authors.initials: P
authors.lastname: Nilsson
authors.forename: Anders
authors.initials: A
authors.lastname: Hallberg
authors.forename: Mats
authors.initials: M
authors.lastname: Larhed