Green and controllable synthesis of symmetrical and unsymmetrical difluoromethylated diarylmethanes via a direct bisarylation strategy enabled by an HFIP-B(C6F5)3 adduct - UTU Research Portal

A1 Refereed original research article in a scientific journal

Green and controllable synthesis of symmetrical and unsymmetrical difluoromethylated diarylmethanes via a direct bisarylation strategy enabled by an HFIP-B(C6F5)3 adduct

Authors: Li, Xindi; Zhu, Yiping; Gong, Zhina; Li, Jinshan; Xie, Jialin; Zhao, Zhendong; Li, Jianwei; Jia, Chunman

Publisher: ROYAL SOC CHEMISTRY

Publishing place: CAMBRIDGE

Publication year: 2024

Journal: Green Chemistry

Journal name in source: GREEN CHEMISTRY

Journal acronym: GREEN CHEM

Volume: 26

Issue: 21

First page : 10969

Last page: 10974

Number of pages: 6

ISSN: 1463-9262

eISSN: 1463-9270

DOI: https://doi.org/10.1039/d4gc03917c

Web address : https://doi.org/10.1039/D4GC03917C

Abstract

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.

Funding information in the publication:
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).