A facile approach for preparing diverse 2,6-disubstituted arylsilanes is reported. Bisfunctionalization such as silylamination and silylsulfanylation of aryne intermediates was efficiently achieved by treating o-iodoaryl triflates with a silylmethyl Grignard reagent in the presence of N-silylamines or S-silyl sulfide, which afforded the corresponding arylsilanes, leaving a broad range of functional groups intact. A simplified procedure using non-silylated amines or a sulfide with chlorosilanes or a silyl triflate allowed the preparation of the desired arylsilanes via a three-component coupling approach, enhancing the convenience of the method.