title: First pinacol coupling in emulsified water: key role of surfactant and impact of alternative activation technologies.
abstract: For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.
authors.affiliation: Sorbonne Universités, Université de Technologie de Compiègne, Ecole Supérieure de Chimie Organique et Minérale, EA 4297 Transformations Intégrées de la Matière Renouvelable, Centre de Recherche Royallieu, CS 60 319, F-60203 Compiègne cedex (France).
authors.forename: Muriel
authors.initials: M
authors.lastname: Billamboz
authors.affiliation: Sorbonne Universités, Université de Technologie de Compiègne, Ecole Supérieure de Chimie Organique et Minérale, EA 4297 Transformations Intégrées de la Matière Renouvelable, Centre de Recherche Royallieu, CS 60 319, F-60203 Compiègne cedex (France). christophe.len@utc.fr.|Department of Chemistry, University of Hull, Hull HU6 7RX (England). christophe.len@utc.fr.
authors.forename: Christophe
authors.initials: C
authors.lastname: Len
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D004655:Emulsions; D006358:Hot Temperature; D008872:Microwaves; D011092:Polyethylene Glycols / Q000737:chemistry*; D013010:Sonication; D013501:Surface-Active Agents / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D000447:Aldehydes; D004655:Emulsions; D013501:Surface-Active Agents; D014867:Water; D011092:Polyethylene Glycols
keywords: C-C coupling reaction; alternative technologies; heterogeneous catalysis; phase-transfer catalysis; surfactants