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IMDN-Tf: Fluoroalkylation-Borylation in a High Regio- and Stereoselective Manner
Vinylboronates and alkylboronates are key components in variegated transformations in all facets of chemical science. IMDN-Tf achieves fluoroalkylation-borylation in one step under mild reaction conditions.
IMDN-Tf (Fig. 1), developed by Prof. Yi Pan of Nanjing University, is a trifluoromethylation reagent which can release trifluoromethyl radicals under photocatalytic conditions. In addition, boron reagent can be activated by the imidazole group , allowing C-B bond and C-CF3 group to be simultaneously introduced into alkynes and non-activated olefins with high regio- and stereoselectivity (Fig. 2). The products can be further transformed into various fluorine-containing frameworks, facilitating the synthesis and subsequent modification of fluorine-containing borides.
Fig. 1 Structural Formula of IMDN-Tf
- IMDN-Tf is a solid compound; It is stable, safe and easy to operate.
- One-step trifluoromethylborylation with mild reaction, no pre-functionalization required.
Fig. 2 Trifluoromethylborylation Reaction
- Various applications: can be further transformed into a series of fluorine-containing functional molecules.
Fig. 3 Further transformations
- “Integrated redox-active reagents for photoinduced regio- and stereoselective fluorocarboborylation”, Weigang Zhang, Zhenlei Zou, Wenxuan Zhao, Shuo Lu, Zhengguang Wu, Mengjun Huang, Xiaochen Wang, Yi Wang, Yong Liang, Yi Zhu, Youxuan Zheng & Yi Pan. Nature Commun. 2020, 11, 2572
Dr. Pan's Profile
Prof. Pan's group mainly focuses on metal-organic materials and organic fluorine chemistry. They are dedicated to the research and development of high-purity metal-organic semiconductor materials, organic photoelectronic materials, new fluorinated reagents and fluoropolymers.