Journal article
The Synthesis of Sulfonyl Fluoride Functionalized 2-Aminothiazoles Using a Diversity Oriented Clicking Strategy
JW Kop, C Hua, DL Priebbenow, CJ Smedley
Organic Letters | AMER CHEMICAL SOC | Published : 2024
Abstract
We present a Diversity Oriented Clicking approach to synthesize a library of novel clickable N-substituted 2-aminothiazoles which serve as versatile hubs for SuFEx click chemistry diversification. Leveraging the spring-loaded reactivity of the 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) connectors, the transformation is simple to perform, tolerant of a wide range of functionality, and regioselective for a single product. Finally, we propose a detailed stepwise reaction mechanism that is supported by experimental and computational analysis.
Grants
Awarded by Monash University
Funding Acknowledgements
C.J.S. thanks the Australian Research Council (ARC) for a Discovery Early Career Research Fellowship (DECRA, DE240100449). D.L.P. also acknowledges the ARC for funding support (DP240100102). The authors thank Monash University for infrastructure and Dr William O'Malley (Monash University) for spectroscopy support.