title: Toward a better understanding on the mechanism of ortholithiation. Tuning of selectivities in the metalation of meta-anisic acid by an appropriate choice of base.
abstract: [reaction: see text] If employed in THF at 0 degrees C, LTMP metalates meta-anisic acid at the doubly activated position. In contrast, n-BuLi/t-BuOK deprotonates position C-4 preferentially at low temperature. Functionalization at C-6 requires protection of the C-2 site beforehand. As a result of these findings, a new mechanism is proposed for the heteroatom-directed ortholithiation of aromatic compounds.
authors.affiliation: Unité de Chimie Organique Moléculaire et Macromoléculaire (UMR 6011), Faculté des Sciences, Université du Maine and CNRS, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.
authors.forename: Thi-Huu
authors.initials: TH
authors.lastname: Nguyen
authors.forename: Nguyet Trang Thanh
authors.initials: NT
authors.lastname: Chau
authors.forename: Anne-Sophie
authors.initials: AS
authors.lastname: Castanet
authors.forename: Kim Phi Phung
authors.initials: KP
authors.lastname: Nguyen
authors.forename: Jacques
authors.initials: J
authors.lastname: Mortier
mesh_terms: D002625:Chemistry, Organic / Q000379:methods; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics; D014641:Vanillic Acid / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D009942:Organometallic Compounds; D008094:Lithium; C056267:3-methoxybenzoic acid; D014641:Vanillic Acid