Photoredox/nickel dual-catalyzed reductive C(sp²)–Si cross-coupling

Abstract

Nickel-catalyzed cross-electrophile coupling of carbon-electrophiles and silicon-electrophiles has recently emerged as a powerful tool for C–Si bond formations to synthesize highly valuable organosilanes. This reductive coupling strategy eliminates the manipulation of highly reactive organometallic reagents, thereby leading to a good functional group tolerance and a high step economy. However, the reported reductive C–Si couplings have to use stoichiometric amounts of Zn or Mn dust as a reductant, which somehow limits the synthetic application. Herein, we reported a novel cross-electrophile coupling of aryl halides with chlorosilanes enabled by dual photoredox/nickel catalysis. Instead of using metallic reductants, a mild and readily available α-silylamine is selected as a reliable organic reductant. Various vinyl chlorosilanes and chlorohydrosilanes were coupled smoothly. This new catalytic protocol offers an alternative approach for facile synthesis of organosilanes.

Keywords

Organosilanes / reductive coupling / organic reductants / photoredox catalysis / nickel catalysis / chlorosilanes

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