- Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity.
Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity.
Organic & biomolecular chemistry (2012-09-15)
Azarmidokht Gholamipour-Shirazi, Christian Rolando
PMID22976369
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.