Design of a Mesoscale Continuous-Flow Route toward Lithiated Methoxyallene

ChemSusChem
Sofie SeghersChristian V Stevens

Abstract

The unique nucleophilic properties of lithiated methoxyallene allow for C-C bond formation with a wide variety of electrophiles, thus introducing an allenic group for further functionalization. This approach has yielded a tremendously broad range of (hetero)cyclic scaffolds, including precursors to active pharmaceutical ingredients. To date, however, its valorization at scale is hampered by the batch synthesis procedure, which suffers from serious safety issues. Hence, the attractive heat- and mass-transfer properties of flow technology were exploited to establish a mesoscale continuous-flow route toward lithiated methoxyallene. An excellent conversion of 94 % was obtained, corresponding to a methoxyallene throughput of 8.2 g h-1 . The process is characterized by short reaction times, mild reaction conditions and a stoichiometric use of reagents.

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Citations

Sep 10, 2019·Chemistry : a European Journal·Marco ColellaRenzo Luisi
Feb 3, 2021·Chemistry : a European Journal·Andreas SimoensSteven P Nolan
Jul 24, 2020·The Journal of Organic Chemistry·Moustapha FortunatoFlorian Jaroschik

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