Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent

Haruo Aikawa, Sakie Tago, Kazuteru Umetsu, Naomichi Haginiwa, Naoki Asao

    Research output: Contribution to journalArticle

    42 Citations (Scopus)

    Abstract

    ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcohols occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel-Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of nucleophiles, such as alcohols, aromatic compounds, and sulfonamides.

    Original languageEnglish
    Pages (from-to)1774-1784
    Number of pages11
    JournalTetrahedron
    Volume65
    Issue number9
    DOIs
    Publication statusPublished - 2009 Feb 28

    Keywords

    • Etherification
    • Friedel-Crafts alkylation
    • Gold catalyst
    • N-Alkylation of sulfonamide
    • Substitution

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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