Issue 40, 2012

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 kAlkylation follows the inverse trend of pKBH+ 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.

Graphical abstract: Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity

Supplementary files

Article information

Article type
Communication
Submitted
30 Jan 2012
Accepted
29 Aug 2012
First published
31 Aug 2012

Org. Biomol. Chem., 2012,10, 8059-8063

Kinetics screening of the N-alkylation of organic superbases using a continuous flow microfluidic device: basicity versus nucleophilicity

A. Gholamipour-Shirazi and C. Rolando, Org. Biomol. Chem., 2012, 10, 8059 DOI: 10.1039/C2OB25215E

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