Palladium-Catalyzed Direct C(sp3)–H Arylations of Benzylsilanes with Aryl Halides

A Pd/Nixantphos-catalyzed cross-coupling reaction between benzylsilanes and aryl halides for the synthesis of diarylmethylsilanes has been developed. This transformation achieves chemoselective deprotonation of simple benzylsilanes at the benzylic position through rarely used CsN(SiMe₃)₂, providing an efficient and straightforward approach to generate a diverse array of diarylmethylsilanes in moderate to good yields. The reaction exhibits excellent functional group tolerance across a broad range of substrates, including electron-rich, -deficient, and -sterically hindered coupling partners. Furthermore, the synthetic practicality of this methodology is illustrated via the synthesis of valuable silane-containing building blocks.