Synlett 2020; 31(16): 1593-1597
DOI: 10.1055/s-0040-1707129
letter

Kinetic Study of Disulfonimide-Catalyzed Cyanosilylation of Aldehydes by Using a Method of Progress Rates

a  School of Chemistry and Molecular Engineering, Frontiers Science Center for Materiobiology and Dynamic Chemistry, East China University of Science & Technology, 130 Meilong Road, Shanghai, 200237, P. R. of China   Email: [email protected]
b  Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
,
Martin Klussmann
b  Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
,
Benjamin List
b  Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany
› Author Affiliations
This work was supported by Shanghai Pujiang Program (18PJ1402200), the National Natural Science Foundation of China (21702059), and the Fundamental Research Funds for the Central Universities (222201814014). We gratefully thank the Max Planck Society, the European Research Council (Advanced Grant ‘High Performance Lewis Acid Organocatalysis, HIPOCAT’ to B.L.), and the Frontiers Science Center for Materiobiology and Dynamic Chemistry, East China University of Science & Technology (JKVJ12001010).


Abstract

Kinetic study of organic reactions, especially multistep catalytic reactions, is crucial to in-depth understanding of reaction mechanisms. Here we report our kinetic study on the chiral disulfonimide-catalyzed cyanosilylation of an aldehyde, which revealed that two molecules of TMSCN are involved in the rate-determining C–C bond-forming step. In addition, the apparent activation energy, enthalpy of activation, and entropy of activation were deduced through a study of the temperature dependence of the reaction rates. More importantly, a novel and efficient method that makes use of the progress rates was developed to treat kinetic data obtained by continuous monitoring of the progress of a reaction by in situ FTIR.

Supporting Information



Publication History

Received: 08 April 2020

Accepted: 28 April 2020

Publication Date:
20 May 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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