Iridium-catalyzed reaction of 1-naphthols, N-(1-naphthyl)benzenesulfonamides, and salicylaldehyde with internal alkynes

1-Naphthols efficiently couple with internal alkynes via cleavage of the C-H bond at the peri-position in the presence of a catalyst system of [IrCl(cod)](2)/PBu'(3) to selectively afford the corresponding 8-vinyl-1-naphthol derivatives. N-(1-Naphthyl)benzenesulfonamides can similarly react with the alkynes. The reaction of salicylaldehyde with the alkynes using the catalyst system gives 2-hydroxyphenyl vinyl ketones via cleavage of the aldehyde C-H bond.