title: Directed remote aromatic metalations: mechanisms and driving forces.
abstract: Directed remote aromatic metalations are useful synthetic transformations allowing for rapid regioselective access to elaborate highly substituted carbocyclic aromatic and heteroaromatic systems. This review unravels the tangle of data reported on directed remote aromatic metalations. Through a careful analysis of critically selected examples, advanced rationalizations of remote metalation regioselectivities are presented. These extend beyond the complex-induced proximity effect (CIPE). Mechanisms, driving forces, and parameters influencing remote metalations are discussed. An understanding of these metalation mechanisms enables more accurate predictability of justification of regiochemical outcomes of these useful synthetic transformations.
authors.affiliation: Eskitis Institute for Cell and Molecular Therapies, Griffith University, Don Young Road, Nathan 4111, Queensland, Australia. dp.tilly@laposte.net
authors.forename: David
authors.initials: D
authors.lastname: Tilly
authors.forename: Jakob
authors.initials: J
authors.lastname: Magolan
authors.forename: Jacques
authors.initials: J
authors.lastname: Mortier
mesh_terms: D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D008670:Metals; D009942:Organometallic Compounds; D008094:Lithium