title: Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity.
abstract: We describe here the determination of the alkylation rate of a set of organic superbases by iodomethane in DMF using a microfluidic continuous flow reactor. Surprisingly, log k(Alkylation) follows the inverse trend of pK(BH+) of the base. Mayr's equation allows a more quantitative approach. From a synthetic point of view, TMGN and BEMP are demonstrated to be the best choices.
authors.affiliation: USR CNRS 3290, Miniaturisation pour la Synthèse, l'Analyse et la Protéomique and FR CNRS 2638 Michel-Eugène Chevreul, Université de Lille 1, Sciences et Technologies, 59655 Villeneuve d'Ascq, France.
authors.forename: Azarmidokht
authors.initials: A
authors.lastname: Gholamipour-Shirazi
authors.forename: Christian
authors.initials: C
authors.lastname: Rolando
mesh_terms: D000478:Alkylation; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D007700:Kinetics; D046210:Microfluidic Analytical Techniques; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*
chemical_list: D006847:Hydrocarbons, Iodinated; D009570:Nitriles; C014055:methyl iodide