Argentination of Fluoroform: Preparation of a Stable AgCF3 Solution with Diverse Reactivities

Jia-Xiang Xiang; Yao Ouyang; Xiu-Hua Xu; Feng-Ling Qing

doi:10.1002/anie.201905782

Argentination of Fluoroform: Preparation of a Stable AgCF₃ Solution with Diverse Reactivities

Angew Chem Int Ed Engl. 2019 Jul 22;58(30):10320-10324. doi: 10.1002/anie.201905782. Epub 2019 Jun 24.

Authors

Jia-Xiang Xiang¹, Yao Ouyang¹, Xiu-Hua Xu¹, Feng-Ling Qing^{1

2}

Affiliations

¹ Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
² Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Lu, Shanghai, 201620, China.

PMID: 31120623
DOI: 10.1002/anie.201905782

Abstract

The transformation of a large-volume industrial by-product and stable greenhouse gas fluoroform (HCF₃ ) to useful products has recently received significant attention. Now, a simple and scalable preparation of AgCF₃ by treatment of HCF₃ with t-BuOK and AgOAc is disclosed. The reactivity of the HCF₃ -derived AgCF₃ has been demonstrated by hydrotrifluoromethylation of alkenes and C-H trifluoromethylation of (hetero)arenes. This work not only provides a new avenue for the utilization of HCF₃ , but also presents a reliable and easy-to-execute synthesis of the relatively stable AgCF₃ solution.

Keywords: alkenes; fluoroform; pentafluoroethylation; silver; trifluoromethylation.

Grants and funding

21332010, 21421002/National Natural Science Foundation of China