Although the reactions of electrophilic Fischer-type metal siloxycarbenes catalytically generated in situ from acylsilanes with a single nucleophile have been documented, the coupling of acylsilanes with two nucleophiles remains unexplored. Herein, we demonstrate that acylsilanes can act as effective cationic carbyne equivalents under visible-light-driven copper catalysis, enabling their coupling with diverse indoles or electron-rich arenes. This strategy operates under mild, redox-neutral conditions and exhibits broad functional group compatibility. Furthermore, the protocol provides a versatile platform for synthesizing symmetric aryl(bisindolyl)methanes and unsymmetric triarylmethane derivatives with high efficiency.