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Selective Acylation of Aryl- and Heteroarylmagnesium Reagents with Esters in Continuous Flow

Martin, Benjamin and Schenkel, Berthold and Ganiek, Maximilian and Djukanovic, Dimitrije and Knochel, Paul and Heinz, Benjamin (2020) Selective Acylation of Aryl- and Heteroarylmagnesium Reagents with Esters in Continuous Flow. Organic Letters, 22 (2). pp. 493-496. ISSN 1523-70601523-7052

Abstract

A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures (-5 to 25 °C) and short residence times (2-10 min) in continuous flow producing various functionalized ketones. The use of flow conditions allows to prevent premature collapse of the hemiacetal intermediates despite non-cryogenic conditions, thus furnishing ketones in good yields. Several ester electrophiles, including ethyl trifluoroacetate, diethyl oxalate and N-heterocyclic esters were suitable substrates for this acylation procedure. Throughout, the coordinating ability of the ester and/or Grignard was found to be a determinant factor in the reaction outcome. This was leveraged by the obtention of several bis-aryl ketones
using 2-hydroxy ester derivatives as substrates

Item Type: Article
Date Deposited: 07 Feb 2020 00:45
Last Modified: 07 Feb 2020 00:45
URI: https://oak.novartis.com/id/eprint/41603

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