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/PBut′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.
Oxidative Cross-Coupling of N-(2′-Phenylphenyl)benzene-sulfonamides or Benzoic and Naphthoic Acids with Alkenes Using a Palladium-Copper Catalyst System under Air
N-(2′-Phenylphenyl)benzenesulfonamides react with acrylate esters accompanied via cleavage of the C-H bond at their 2′-position in the presence of a catalyst system of Pd(OAc)2 and Cu(OAc)2 and a base under air to produce 5,6-dihydro-5-(benzenesulfonyl)phenanthridine-6-acetate derivatives in high yields. The reactions of benzoic acid with butyl acrylate and styrene can also give 3-[(butoxycarbonyl)methyl]phthalide and 3-phenylisocoumarin, respectively.