Dearomative Insertion of Fluoroalkyl Carbenes into Azoles Leading to Fluoroalkyl Heterocycles with a Quaternary Center
Linxuan Li
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
These authors contributed equally to this work.
Search for more papers by this authorYongquan Ning
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
These authors contributed equally to this work.
Search for more papers by this authorHongzhu Chen
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
These authors contributed equally to this work.
Search for more papers by this authorYongyue Ning
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorDr. Paramasivam Sivaguru
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorPeiqiu Liao
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorQingwen Zhu
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorYong Ji
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorGraham de Ruiter
Schulich Faculty of Chemistry, Technion Israel Institute of Technology, Technion City, 3200008 Haifa, Israel
Search for more papers by this authorCorresponding Author
Prof. Xihe Bi
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorLinxuan Li
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
These authors contributed equally to this work.
Search for more papers by this authorYongquan Ning
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
These authors contributed equally to this work.
Search for more papers by this authorHongzhu Chen
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
These authors contributed equally to this work.
Search for more papers by this authorYongyue Ning
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorDr. Paramasivam Sivaguru
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorPeiqiu Liao
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorQingwen Zhu
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorYong Ji
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
Search for more papers by this authorGraham de Ruiter
Schulich Faculty of Chemistry, Technion Israel Institute of Technology, Technion City, 3200008 Haifa, Israel
Search for more papers by this authorCorresponding Author
Prof. Xihe Bi
Department of Chemistry, Northeast Normal University, Changchun, 130024 China
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorAbstract
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.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
The data that support the findings of this study are available from the corresponding author upon reasonable request.
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