title: Combined directed ortho metalation-halogen dance (HD) synthetic strategies. HD-anionic ortho fries rearrangement and double HD sequences.
abstract: A general and efficient directed ortho metalation (DoM)-halogen dance (HD)-electrophile quench sequence for the synthesis of trisubstituted pyridyl O-carbamates is described. A second HD sequence furnishes highly functionalized tetrasubstituted pyridines. Furthermore, a hitherto unobserved double HD rearrangement is reported. Under similar LDA conditions, aromatic O-carbamates with OMe, Cl, and F substituents (4a-c) undergo either a HD-electrophile quench sequence, 4a-c --> 18-20, or a HD-anionic ortho Fries rearrangement, 4a-c --> 6a-c, respectively.
authors.affiliation: Fachbereich Chemie and Konstanz Research School of Chemical Biology, Universität Konstanz, Fach 720, D-78457 Konstanz, Germany.
authors.forename: Ricarda E
authors.initials: RE
authors.lastname: Miller
authors.forename: Toni
authors.initials: T
authors.lastname: Rantanen
authors.forename: Kevin A
authors.initials: KA
authors.lastname: Ogilvie
authors.forename: Ulrich
authors.initials: U
authors.lastname: Groth
authors.forename: Victor
authors.initials: V
authors.lastname: Snieckus
mesh_terms: D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002219:Carbamates