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Ethyl lithiodiazoacetate: extremely unstable intermediate handled efficiently in flow

Müller, Simon T. R., Hokamp, Tobias, Ehrmann, Svenja, Hellier, Paul and Wirth, Thomas 2016. Ethyl lithiodiazoacetate: extremely unstable intermediate handled efficiently in flow. Chemistry: A European Journal 22 (34) , pp. 11940-11942. 10.1002/chem.201602133

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Abstract

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 diisopropylamide (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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Wiley
ISSN: 0947-6539
Date of First Compliant Deposit: 10 August 2016
Date of Acceptance: 24 June 2016
Last Modified: 14 Jun 2018 03:07
URI: http://orca.cf.ac.uk/id/eprint/93710

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