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Synlett 2020; 31(16): 1593-1597
DOI: 10.1055/s-0040-1707129
DOI: 10.1055/s-0040-1707129
letter
Kinetic Study of Disulfonimide-Catalyzed Cyanosilylation of Aldehydes by Using a Method of Progress Rates
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
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707129.
- Supporting Information
Publication History
Received: 08 April 2020
Accepted: 28 April 2020
Article published online:
20 May 2020
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