Palladium-catalyzed carbon-carbon bond forming reactions

A method of forming an enone of formula:

• wherein R and R′ are independently hydrogen;
• cyclic or acyclic, substituted or unsubstituted, branched or unbranched aliphatic;
• cyclic or acyclic, substituted or unsubstituted, branched or unbranched heteroaliphatic;
• substituted or unsubstituted, branched or unbranched acyl;
• substituted or unsubstituted, branched or unbranched aryl;
• substituted or unsubstituted, branched or unbranched heteroaryl;
• —ORA;
• ═O;
• —C(═O)RA;
• —CO2RA;
• —CN;
• —SCN;
• —SRA;
• —SORA;
• —SO2RA;
• —NO2;
• —N(RA)2;
• —NHC(O)RA;
• or —C(RA)3;
• wherein each occurrence of RA is independently a hydrogen, a protecting group, an aliphatic moiety, a heteroaliphatic moiety, an acyl moiety;
• an aryl moiety;
• a heteroaryl moiety;
• alkoxy;
• aryloxy;
• alkylthio;
• arylthio;
• amino, alkylamino, dialkylamino, heteroaryloxy;
• or heteroarylthio moiety, the method comprising steps of:
• providing a terminal alkyne of formula:
• providing an alkene of formula:
• reacting the alkyne and alkene in the presence of palladium(II) under suitable conditions to form an enone, wherein the oxygen of the carbonyl group of the enone is derived from water, and wherein none of the carbon or oxygen atoms in the enone are derived from carbon monoxide.