Scope of the benzoic acid derivatives^a.

^aReaction conditions: 3 or 4 (0.2 mmol, 1 equiv.), TMB (1.75 equiv.), a palladium catalyst, a phosphine ligand and CsF (2 equiv.) in dioxane (0.6 mL) at 160 °C for 24 h under N₂. Isolated yields. For amides, [Pd(allyl)Cl]₂ (5 mol%) and dppb (20 mol%) were used. For esters, Pd(OAc)₂ (10 mol%) and dcype (20 mol%) were used.

^bGC yield (internal standard: diphenylacetylene).

^cEt₃N (2 equiv.) was added.

^dGC yield (internal standard: mesitylene). dcype = 1,2-bis(dicyclohexylphosphino)ethane.