Development of highly active organocatalyst by use of fluorogenic probes for chemical transformations

2014 Fiscal Year Final Research Report

• Project/Area Number: 23685035
• Research Category: Grant-in-Aid for Young Scientists (A)
• Allocation Type: Single-year Grants
• Research Field: Environmental chemistry
• Research Institution: Shizuoka University
• Principal Investigator: MASE NOBUYUKI 静岡大学, 工学研究科, 教授 (40313936)
• Project Period (FY): 2011-04-01 – 2015-03-31
• Keywords: 化学結合形成検出用センサー / 蛍光センサー / OFF-ONセンサー / 触媒探索 / 環境調和型触媒 / 有機分子触媒 / エナミン触媒 / イミニウム触媒

Outline of Final Research Achievements

Fluorogenic substrates or probes for chemical transformations, molecules that show no or very low fluorescence but show high fluorescence upon chemical transformations, are useful for monitoring the progress of chemical transformations, especially at the initial stages of the reaction. Assays using fluorogenic substrates accelerate the identification of superior catalysts and reaction conditions in high-throughput formats as well as characterization of catalysis on a small scale. Here, we studied the development of aldehyde, imine, and enals-type fluorogenic probes and their use in monitoring various organocatalytic chemical transformations, including C-C bond-forming reactions such as aldol, Mannich, and Diels-Alder reactions. The best combinations of amine catalyst and acid additive in both enamine and iminium catalysis were identified. In conclusion, we have developed fluorogenic compounds that can be used for rapid monitoring chemical reactions through increased fluorescence.

Free Research Field

有機化学