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A rhodium(III)‐catalyzed oxidative cyclization of chalcones with internal alkynes is reported, generating biologically important 3,3‐disubstituted 1‐indanones along with reusable aromatic aldehydes. This transformation features unique (4+1) reaction mode, excellent regioselectivity in alkyne insertion, broad substrate scope, allows for the construction of quaternary carbon centers, and is scalable...