Tertiary C(sp3)–Si Bond Formation via Reactivity Umpolung of Silyl Reagents
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A transition-metal-free decyanative silylation of malononitriles with silyl chlorides enabled by a silyl umpolung strategy is described. This reaction involves NaOtBu-promoted silylboranes addition to malononitriles to generate electrophilic silyl cyanide and nucleophilic ketenimine intermediates in situ, which recombine to form sterically congested C(sp3)–Si bonds. This method expands silylborane reactivity and provides a general route to alkylsilanes.
