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Practical Application of the Aqueous 'Sulfonyl-Azide-Free' (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters

Dmitry Dar'in, Grigory Kantin, Mikhail Krasavin*

*Saint Petersburg State University, Saint Petersburg, 199034, Russian Federation, Email: m.krasavinspbu.ru

D. Dar'in, G. Kantin, M. Krasavin, Synthesis, 2019, 51, 4284-4292.

DOI: 10.1055/s-0039-1690613 (free Supporting Information)


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Abstract

A 'sulfonyl-azide-free' ('SAFE') protocol for diazo transfer to CH-acidic 1,3-dicarbonyl compounds has been extended to less reactive monocarbonyl substrates. In situ formylation, followed by the addition of an optimized amount of a mixture of sodium azide, potassium carbonate, and m-carboxybenzenesulfonyl chloride in water (SAFE cocktail) led to the formation of the desired diazo compounds.

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Key Words

diazo transfer, water solubility, formylation, deformylation, C-H acidity


ID: J66-Y2019