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Rapid generation and safe use of carbenes enabled by a novel flow protocol with in-line IR spectroscopy

Muller, Simon T. R., Murat, Aurélien, Maillos, Delphine, Lesimple, Patrick, Hellier, Paul and Wirth, Thomas 2015. Rapid generation and safe use of carbenes enabled by a novel flow protocol with in-line IR spectroscopy. Chemistry - A European Journal 21 (19) , pp. 7016-7020. 10.1002/chem.201500416

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Abstract

A powerful new continuous process for the formation and use of donor/acceptor-substituted carbenes is described. The safety profile of diazo group transfer on methyl phenylacetate was determined including kinetic studies in batch and in flow using in-line IR analysis. Batch work-up and liquid chromatography were circumvented by developing an optimized liquid/liquid flow separation method providing aryl diazoacetates in high purity. Fast screening of reaction conditions in flow with in-line IR analysis allowed rapid reaction optimization. Finally, a multistep process of diazo group transfer, extraction, separation and subsequent diazo decomposition combined with multiple X[BOND]H insertion reactions was established.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Wiley
ISSN: 0947-6539
Last Modified: 07 Feb 2020 15:45
URI: http://orca-mwe.cf.ac.uk/id/eprint/71953

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