I've done a very similar reaction to the one below but by TLC I observe only starting materials. It's super clear that nothing else is going on. Conditions: K3PO4, Pd(dppf)Cl2, dioxane/water, heat to 100 deg.C.
What thoughts do you have on why this doesn't work?
I imagine the alkyne chelating to the Pd and potentially 'poisoning' it? I currently lack the words and technical lingo to put this into a formal explanation.
A competing Sonogashira perhaps? Unlikely given the aqueous conditions.
Any other issues?