Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 3, Pages 557-568Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707259
Keywords
heterocycles; flow chemistry; organolithiums; Barbier reaction; halogen-lithium exchange
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Funding
- FAPESP [2018/08856-5]
- German Academic Scholarship Foundation
- Deutsche Forschungsgemeinschaft
- Ludwig-Maximilians-Universitat Munchen
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This method involves a halogen-lithium exchange reaction of (hetero)aromatic halides in the presence of various electrophiles, resulting in the formation of polyfunctional (hetero)arenes. The use of a flow set-up allows for the instant trapping of organolithiums with electrophiles, enabling the functionalization of (hetero)arenes containing highly sensitive functional groups such as esters that are not tolerated in batch conditions.
A halogen-lithium exchange reaction of (hetero)aromatic halides performed in the presence of various electrophiles such as aldehydes, ketones, Weinreb amides, and imines using BuLi as exchange reagent and a commercially available flow set-up is reported. The organolithiums generated in situ were instantaneously trapped with various electrophiles (Barbier conditions) resulting in the formation of polyfunctional (hetero)arenes. This method enables the functionalization of (hetero)arenes containing highly sensitive functional groups such as esters, which are not tolerated in batch conditions.
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