Ethyl Lithiodiazoacetate: Extremely unstable intermediate handled efficiently in flow

    Simon T. R. Müllera, Tobias Hokampa, Svenja Ehrmanna, Paul Hellierb, Thomas Wirtha

    • a Cardiff University School of Chemistry Cardiff UK
    • b Parc Industriel de la Chartreuse Pierre Fabre Médicament Castres CEDEX France

    Ethyl diazoacetate(EDA) is one of the most prominent diazo reagents. It is frequently used in metal–carbene-type reactions. However, EDA can also be used as a nucleophile under base catalysis. Whilst the addition of EDA to aldehydes can be performed using organic bases, the addition of EDA to other carbonyl electrophiles requires the use of organometallics such as lithium diisopro-pylamide (LDA). The generated ethyl lithiodiazoacetate is highly reactive and decomposes rapidly, even at low temperatures. Herein, we report a continuous flow protocol that overcomes the problems associated with the instantaneous decomposition of ethyl lithiodiazoacetate. The addition of ethyl lithiodiazoacetate to ketones provides direct access to tertiary diazoalcohols in good yields.

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