Decarbonylative coupling reaction of aromatic esters

Ryota Isshiki, Toshimasa Okita, Kei Muto, Junichiro Yamaguchi

    Research output: Contribution to journalReview article

    Abstract

    Transition metal-catalyzed cross-coupling reactions are a powerful method to form chemical bonds. Conventionally, haloarenes has been used as the most reliable aryl electrophiles in cross- coupling. Recent studies in the cross-coupling arena have enabled to employ unconventional but ubiquitous aryl electrophiles such as phenol and aniline. With this trend of organic synthesis, cross-coupling reactions using aromatic carboxylic acid derivatives such as esters as aryl electrophiles have gained considerable attention as a de novo and efficient method to construct C-C and C-heteroatom bonds. In order to realize this particular transformation, it is important to develop and design transition metal catalysts, those are active toward the scission of ester C-O bonds and decarbonylation. In this review, we describe the progress of catalytic decarbonylative cross- coupling of aromatic esters including chronological aspects and mechanistic considerations.

    Original languageEnglish
    Pages (from-to)300-314
    Number of pages15
    JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
    Volume76
    Issue number4
    DOIs
    Publication statusPublished - 2018 Jan 1

    Fingerprint

    Transition metals
    Esters
    Chemical bonds
    Carboxylic Acids
    Phenol
    Carboxylic acids
    Derivatives
    Catalysts
    aniline
    calcium ascorbate

    Keywords

    • Aromatic esters
    • Cross-coupling
    • Decarbonylative
    • Transition metal catalyst

    ASJC Scopus subject areas

    • Organic Chemistry

    Cite this

    Decarbonylative coupling reaction of aromatic esters. / Isshiki, Ryota; Okita, Toshimasa; Muto, Kei; Yamaguchi, Junichiro.

    In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 76, No. 4, 01.01.2018, p. 300-314.

    Research output: Contribution to journalReview article

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    AU - Okita, Toshimasa

    AU - Muto, Kei

    AU - Yamaguchi, Junichiro

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    AB - Transition metal-catalyzed cross-coupling reactions are a powerful method to form chemical bonds. Conventionally, haloarenes has been used as the most reliable aryl electrophiles in cross- coupling. Recent studies in the cross-coupling arena have enabled to employ unconventional but ubiquitous aryl electrophiles such as phenol and aniline. With this trend of organic synthesis, cross-coupling reactions using aromatic carboxylic acid derivatives such as esters as aryl electrophiles have gained considerable attention as a de novo and efficient method to construct C-C and C-heteroatom bonds. In order to realize this particular transformation, it is important to develop and design transition metal catalysts, those are active toward the scission of ester C-O bonds and decarbonylation. In this review, we describe the progress of catalytic decarbonylative cross- coupling of aromatic esters including chronological aspects and mechanistic considerations.

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