Synlett 2016; 27(10): 1486-1510
DOI: 10.1055/s-0035-1561379
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© Georg Thieme Verlag Stuttgart · New York

Deployment of Small-Ring Azaheterocycles as Building Blocks for the Synthesis of Organofluorine Compounds

Jeroen Dolfen
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, 9000 Ghent, Belgium   Email: norbert.dekimpe@UGent.be   Email: matthias.dhooghe@UGent.be
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Norbert De Kimpe*
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, 9000 Ghent, Belgium   Email: norbert.dekimpe@UGent.be   Email: matthias.dhooghe@UGent.be
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Matthias D’hooghe*
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, 9000 Ghent, Belgium   Email: norbert.dekimpe@UGent.be   Email: matthias.dhooghe@UGent.be
› Author Affiliations
Further Information

Publication History

Received: 03 December 2015

Accepted after revision: 14 January 2016

Publication Date:
10 March 2016 (online)


Abstract

This account describes the endeavors made by our group concerning the synthesis of aziridines and azetidin(on)es and their use as novel building blocks for the preparation of nitrogen-containing organofluorine compounds. The majority of contributions, covered in the first part, comprises the study of fluorinated small-ring substrates, focusing on both their synthesis and their synthetic applicability for further transformations. These investigations revealed a pronounced effect of fluorine on the overall reactivity of small-ring azaheterocycles, often resulting in a different behavior compared with that of their nonfluorinated counterparts. In the second part, contributions are covered dealing with the transformation of nonfluorinated small rings into fluorinated target molecules upon treatment with fluorinated reagents.

1 Introduction

2 Synthesis and Reactivity of Fluorine-Containing Aziridines and Azetidines

2.1 Aziridines

2.2 Azetidines

3 Synthesis of Fluorine-Containing Nitrogen Compounds Starting from Nonfluorinated Aziridines and Azetidines

3.1 Aziridines

3.2 Azetidines

4 Conclusion and Outlook

 
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