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A metal‐free tunable 1,2‐difunctionalization of the terminal alkynes showcasing a tandem installation of C−C and C−S bonds has been developed. The key enabling factor for the approach is the use of acetic acid as an acyl source to synthesize β‐substituted α,β‐unsaturated ketones. The reaction at room temperature leads to the regioselective acylation at the terminal carbon of alkynes, whereas at −78 °C, the acylation occurs at the more substituted carbon. [ABSTRACT FROM AUTHOR]