Ethyl lithiodiazoacetate: extremely unstable intermediate handled efficiently in flow

Müller, Simon T. R., Hokamp, Tobias, Ehrmann, Svenja, Hellier, Paul and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 2016. Ethyl lithiodiazoacetate: extremely unstable intermediate handled efficiently in flow. Chemistry: A European Journal 22 (34) , pp. 11940-11942. 10.1002/chem.201602133

Preview

PDF - Accepted Post-Print Version Download (342kB) | Preview

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:	03 Dec 2024 12:30
URI:	https://orca.cardiff.ac.uk/id/eprint/93710

Citation Data

Cited 18 times in Scopus. View in Scopus. Powered By Scopus® Data

Actions (repository staff only)

Edit Item