Method for regioselective hydroalkylation of terminal alkyne
Here is a potential solution using old-school chemistry, though with several steps.

Hydroborate the alkyne and work up with $\ce{H2O2}$ to give the aldehyde.

Alkylate the aldehyde enolate with $\ce{RI}$, either directly (LDA or LiHMDS) or via enamine/silyl enol ether

Reduce aldehyde to alcohol ($\ce{NaBH4/EtOH}$)

Form triflate/mesylate and eliminate (DBU/Toluene, reflux)


If you wish to explore @orthocresol's suggestion of enol triflate coupling then coupling the triflate with the cuprate of your alkyl chain looks to be viable according to this Tet. Lett. article from McMurry and Scott1
References

John E. McMurry, William J. Scott, “A new method of olefin synthesis. Coupling of lithium dialkylcuprates with enol triflates,” Tetrahedron Letters 1980, 21(45), 4313-4316, DOI: 10.1016/S0040-4039(00)77845-2