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Dearomative Insertion of Fluoroalkyl Carbenes into Azoles Leading to Fluoroalkyl Heterocycles with a Quaternary Center.
- Source :
- Angewandte Chemie; 1/2/2024, Vol. 136 Issue 1, p1-10, 10p
- Publication Year :
- 2024
-
Abstract
- The skeletal ring expansion of heteroarenes through carbene insertion is gaining popularity in synthetic chemistry. Efficient strategies for heterocyclic ring expansion to access heterocycles containing a fluoroalkyl quaternary carbon center through fluoroalkyl carbene insertion are highly desirable because of their broad applications in medicinal chemistry. Herein, we report a general strategy for the dearomative one‐carbon insertion of azoles using fluoroalkyl N‐triftosylhydrazones as fluoroalkyl carbene precursors, resulting in ring‐expanded heterocycles in excellent yields with good functional‐group compatibility. The broad generality of this methodology in the late‐stage diversification of pharmaceutically interesting bioactive molecules and versatile transformations of the products has been demonstrated. [ABSTRACT FROM AUTHOR]
- Subjects :
- HETEROCYCLIC compounds
CARBENES
PHARMACEUTICAL chemistry
HETEROARENES
AZOLES
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 136
- Issue :
- 1
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 174515628
- Full Text :
- https://doi.org/10.1002/ange.202313807