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

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 in...

Full description

Saved in:
Bibliographic Details
Published inSynlett Vol. 31; no. 16; pp. 1593 - 1597
Main Authors Zhang, Zhipeng, Klussmann, Martin, List, Benjamin
Format Journal Article
LanguageEnglish
Published Rüdigerstraße 14, 70469 Stuttgart, Germany Georg Thieme Verlag KG 01.10.2020
Subjects
letter
organocatalysis
cyanation
aldehydes
progress rates
kinetics
disulfonimides
Online AccessGet full text

Cover

More Information
Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1707129