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Generation of ynolates via reductive lithiation using flow microreactors

Author:
Umezu, Satoshi, Yoshiiwa, Toshiya, Tokeshi, Manabu, Shindo, Mitsuru
Source:
Tetrahedron letters 2014 v.55 pp. 1822-1825
ISSN:
0040-4039
Subject:
ambient temperature, batch systems, carbonyl compounds, chemical reactions, chemical structure, lithium, methodology
Abstract:
A new method has been developed for the generation and subsequent reaction of ynolates in a micro flow reactor system. This new procedure allowed for ynolates to be prepared at 0°C or ambient temperature within 1min via a reductive lithiation reaction, whereas the corresponding batch processes generally require low temperature control and extended reaction times of up to 1h. The resulting ynolates were applied to the olefination of carbonyl compounds, with the reactions reaching completion in a much shorter reaction time in the continuous flow reactor than the batch reactor. These results highlight the practical utility of the ynolate reaction, and represent the first reported example of the use of lithium naphthalenide in a flow microreactor, which would contribute to progress of the flash chemistry.
Agid:
5516167