title: Multicomponent, flow diazotization/Mizoroki-Heck coupling protocol: dispelling myths about working with diazonium salts.
abstract: A single pass flow diazotization/Mizoroki-Heck protocol has been developed for the production of cinnimoyl and styryl products. The factors that govern aryl diazonium salt stability have been examined in detail leading to the development of a MeOH/DMF co-solvent system in which the diazonium salts can be generated in the presence of all other reaction components and then coupled selectively to give the desired products. Finally the key role of the reaction quench for flow reactions has been demonstrated.
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J1P3 (Canada).
authors.forename: Kumara S
authors.initials: KS
authors.lastname: Nalivela
authors.forename: Michael
authors.initials: M
authors.lastname: Tilley
authors.forename: Michael A
authors.initials: MA
authors.lastname: McGuire
authors.forename: Michael G
authors.initials: MG
authors.lastname: Organ
mesh_terms: D003979:Diazonium Compounds / Q000737:chemistry*; D004126:Dimethylformamide / Q000737:chemistry; D000432:Methanol / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D012995:Solubility; D013696:Temperature
chemical_list: D003979:Diazonium Compounds; D012492:Salts; D004126:Dimethylformamide; D000432:Methanol
keywords: Heck reaction; cross-coupling; diazonium salts; flow; microreactors