Nickel-catalyzed alkyl-arylation of 3,3,3-trifluoropropene

Chang Xu; Ming-Kuan Wang; Shu Zhang; Xingang Zhang

doi:10.1038/s42004-022-00659-7

Nickel-catalyzed alkyl-arylation of 3,3,3-trifluoropropene

Commun Chem. 2022 Mar 22;5(1):41. doi: 10.1038/s42004-022-00659-7.

Authors

Chang Xu^#¹, Ming-Kuan Wang^#¹, Shu Zhang², Xingang Zhang³

Affiliations

¹ Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
² The Yangtze Delta Region Institute (Huzhou), University of Electronic Science and Technology of China, Huzhou, 313001, China.
³ Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China. xgzhang@mail.sioc.ac.cn.

^# Contributed equally.

Abstract

Owing to the versatile synthetic utility of its carbon-carbon double bond, low-cost industrial chemical 3,3,3-trifluoropropene (TFP) represents one of the most straightforward and cost-efficient precursors to prepare trifluoromethylated compounds. However, only limited methods for the efficient transformations of TFP have been reported so far. Here, we report a nickel-catalyzed dicarbofunctionalization of TFP. The reaction uses inexpensive NiCl₂·6H₂O as the catalyst and 4,4'-biMeO-bpy and PCy₂Ph as the ligands, allowing the alkyl-arylation of TFP with a variety of tertiary alkyl iodides and arylzinc reagents in high efficiency. This nickel-catalyzed process overcomes the previous challenges by suppressing β-H and β-F eliminations from TFP, rendering this strategy effective for the transformations of TFP into medicinal interest trifluoromethylated compounds.

Abstract

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