Synlett 2020; 31(16): 1593-1597
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:
zhipengzhang@ecust.edu.cn
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
› Institutsangaben 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.
Key words
kinetics -
progress rates -
disulfonimides -
cyanation -
organocatalysis -
aldehydes
Supporting Information
Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707129.
Supporting Information
Publikationsverlauf
Eingereicht: 08. April 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
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ChemRxiv 2020; preprint DOI: 10.26434/chemrxiv.12084768.v1
