A gold-catalyzed alkylation of alcohols and aromatic compounds is described. The reaction of ortho-alkynylbenzoic acid alkyl esters with alcohols or aromatic compounds occurs in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce corresponding ethers or Friedel-Crafts alkylation products in good to high yields. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of alcohols or aromatic compounds.

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Etherification O 0328Gold-Catalyzed Etherification and Friedel-Crafts Alkylation Using ortho--Alkynylbenzoic Acid Alkyl Ester as an Efficient Alkylating Agent. -The mild conditions allow the preparation of a variety of title compounds including. intramolecular versions. The presence of an ortho-alkynyl group is crucial for the reaction. The isocoumarin by-products are eliminated in quantitative yields. -(ASAO*, N.; AIKAWA, H.; TAGO, S.; UMETSU, K.; Org. Lett. 9 (2007) 21, 4299-4302; Dep. Chem., Grad. Sch. Sci., Tohoku Univ., Aoba, Sendai 980, Japan; Eng.) -R. Steudel 13-049

N-Alkylation O 0268Gold-Catalyzed Substitution Reaction with ortho-Alkynylbenzoic Acid Alkyl Ester as an Efficient Alkylating Agent. -The recently published method for the synthesis of ethers and Friedel-Crafts alkylation products is extended to the inter-and intramolecular N-alkylation of sulfonamides. In addition, a detailed study on the recently reported results is given. -(AIKAWA, H.; TAGO, S.; UMETSU, K.; HAGINIWA, N.; ASAO*, N.; Tetrahedron 65 (2009) 9, 1774-1784; Dep. Chem., Grad. Sch. Sci., Tohoku Univ., Aoba, Sendai 980, Japan; Eng.) -Klein