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

Azarmidokht Gholamipour-Shirazi; Christian Rolando

doi:10.1039/C2OB25215E

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Organic & Biomolecular Chemistry

Issue 40, 2012

The international home of synthetic, physical and biomolecular organic chemistry.

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

Azarmidokht Gholamipour-Shirazi^a and Christian Rolando*^a

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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
E-mail: christian.rolando@univ-lille1.fr ;
Fax: +33 (0)3 20 33 61 36 ;
Tel: +33 (0)3 20 43 49 77

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

DOI: 10.1039/C2OB25215E
Received 30 Jan 2012, Accepted 29 Aug 2012
First published online 31 Aug 2012

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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.

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

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