Green and controllable synthesis of symmetrical and unsymmetrical difluoromethylated diarylmethanes via a direct bisarylation strategy enabled by an HFIP-B(C6F5)3 adduct
: Li, Xindi; Zhu, Yiping; Gong, Zhina; Li, Jinshan; Xie, Jialin; Zhao, Zhendong; Li, Jianwei; Jia, Chunman
Publisher: ROYAL SOC CHEMISTRY
: CAMBRIDGE
: 2024
: Green Chemistry
: GREEN CHEMISTRY
: GREEN CHEM
: 26
: 21
: 10969
: 10974
: 6
: 1463-9262
: 1463-9270
DOI: https://doi.org/10.1039/d4gc03917c
: https://doi.org/10.1039/D4GC03917C
A metal-free B(C6F5)(3) and HFIP synergistically catalyzed bisarylation reaction between difluoroacetaldehyde ethyl hemiacetal and anilines was developed to efficiently synthesize symmetrical and unsymmetrical difluoromethylated diarylmethanes without using stoichiometric activating agents or in concentrated strong acid media. This efficient, scalable and operationally simple protocol displays high atom economy and broad substrate tolerance, allowing quick access to diverse symmetrical and unsymmetrical difluoromethylated diarylmethane products under mild conditions. Furthermore, the recyclability and reusability of the HFIP solvent make the reaction environmentally friendly.
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We are grateful for the financial support from the National Natural Science Foundation of China (22161017 and 22161016), Innovational Fund for Scientific and Technological Personnel of Hainan Province (KJRC2023D34) and the Start-up Research Foundation of Hainan University (KYQD(ZR)23166).
