Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp²)–H Bonds Enabled by Cobalt Catalysis

We report a chelation-assisted C–H arylation of various indoles with sterically and electronically diverse (hetero)­arylsilanes enabled by cost-effective Cp*-free cobalt catalysis. Key to the success of this strategy is the judicious choice of copper­(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodology features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and late-stage diversification of biologically active molecules.