Homologation Reaction of Ketones with Diazo Compounds

Nuno R. Candeias, Roberta Paterna, Pedro M. P. Gois

    Research output: Contribution to journalReview Articlepeer-review

    306 Citations (Scopus)

    Abstract

    This review covers the addition of diazo compounds to ketones to afford homologated ketones, either in the presence or in the absence of promoters or catalysts. Reactions with diazoalkanes, aryldiazomethanes, trimethylsilyldiazomethane, α-diazo esters, and disubstituted diazo compounds are covered, commenting on the complex regiochemistry of the reaction and the nature of the catalysts and promoters. The recent reports on the enantioselective version of ketone homologation reactions are gathered in one section, followed by reports on the use of cyclic ketones ring expansion in total synthesis. Although the first reports of this reaction appeared in the literature almost one century ago, the recent achievements, in particular, for the asymmetric version, forecast the development of new breakthroughs in the synthetically valuable field of diazo chemistry.
    Original languageEnglish
    Pages (from-to)2937-2981
    Number of pages45
    JournalChemical Reviews
    Volume116
    Issue number5
    DOIs
    Publication statusPublished - 2016
    Publication typeA2 Review article in a scientific journal

    Publication forum classification

    • Publication forum level 2

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