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Harenberg, Johannes H.; Weidmann, Niels; Wiegand, Alexander J.; Hoefer, Carla A.; Annapureddy, Rajasekar Reddy ORCID logoORCID: https://orcid.org/0000-0001-5855-4688 und Knochel, Paul ORCID logoORCID: https://orcid.org/0000-0001-7913-4332 (2021): (2‐Ethylhexyl)sodium: A Hexane‐Soluble Reagent for Br/Na‐Exchanges and Directed Metalations in Continuous Flow. In: Angewandte Chemie International Edition, Bd. 60, Nr. 26: S. 14296-14301 [PDF, 2MB]

Abstract

We report the on-demand generation of hexane-soluble (2-ethylhexyl)sodium (1) from 3-(chloromethyl)heptane (2) using a sodium-packed-bed reactor under continuous flow conditions. Thus, the resulting solution of 1 is free of elemental sodium and therefore suited for a range of synthetic applications. This new procedure avoids the storage of an alkylsodium and limits the handling of metallic sodium to a minimum. (2-Ethylhexyl)sodium (1) proved to be a very useful reagent and undergoes in-line Br/Na-exchanges as well as directed sodiations. The resulting arylsodium intermediates are subsequently trapped in batch with various electrophiles such as ketones, aldehydes, Weinreb-amides, imines, allyl bromides, disulfides and alkyl iodides. A reaction scale-up of the Br/Na-exchange using an in-line electrophile quench was also reported.

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