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Reductive cross-coupling reactions involving two electrophilic reagents have become increasingly important in modern synthetic chemistry. Previous studies have investigated electrophilic reagents featuring zero or one inactive bond; however, reactions involving electrophilic reagents with two inactive bonds remain unexplored. This study presents the first nickel-catalyzed reductive cross-coupling reaction under mechanical conditions, involving aryl ethers and aryl fluorides, both of which contain inactive bonds. The reaction successfully synthesized a series of multifunctional biphenyl compounds, specifically including several sparingly soluble substrates that are challenging to prepare in a solvent system. Mechanistic studies have demonstrated that nickel and magnesium play a crucial role in the activation of C─F bonds. This novel coupling reaction offers a beneficial approach for polymer degradation and the development of luminescent materials.
Liu et al. (Tue,) studied this question.