Continuous Flow as Enabling Technology: Synthesis of Heteroaromatic Sulfinates as Bench Stable Cross-Coupling Partners

An enabling continuous flow setup for handling of unstable organolithium intermediates and synthesis of heteroaryl sulfinates on a multigram scale is described. The developed continuous flow process allows for the synthesis and simple isolation of heteroaryl sulfinates which are otherwise challengin...

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Bibliographic Details
Published in:Organic letters 2020-08, Vol.22 (15), p.6082-6085
Main Authors: Lima, Fabio, André, Jérôme, Marziale, Alexander, Greb, Andreas, Glowienke, Susanne, Meisenbach, Mark, Schenkel, Berthold, Martin, Benjamin, Sedelmeier, Joerg
Format: Article
Language:English
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Summary:An enabling continuous flow setup for handling of unstable organolithium intermediates and synthesis of heteroaryl sulfinates on a multigram scale is described. The developed continuous flow process allows for the synthesis and simple isolation of heteroaryl sulfinates which are otherwise challenging to access in classical batch mode. The lithium sulfinate salts prepared by this method were shown to be efficient reaction partners in palladium catalyzed C­(sp 2)–C­(sp 2) cross-coupling to access medicinally relevant bis-heteroaryl motifs.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02155