Iron-catalyzed Alkyl–Alkyl Negishi Coupling of Organoaluminum Reagents

The first iron-catalyzed cross-coupling reaction of alkyl halides with alkylaluminum reagents (alkyl–alkyl Negishi coupling) is developed using an iron/bisphosphine catalyst system. The reaction shows high functional group tolerance: various primary alkyl halides possessing a non-protected indole, c...

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Bibliographic Details
Published in:Chemistry letters 2019-03, Vol.48 (3), p.238-241
Main Authors: Agata, Ryosuke, Kawamura, Shintaro, Isozaki, Katsuhiro, Nakamura, Masaharu
Format: Article
Language:English
Subjects:
Catalysis
Catalysts
Chemical reactions
Cross coupling
Functional groups
Halides
Iron
Potassium fluoride
Reagents
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Summary:The first iron-catalyzed cross-coupling reaction of alkyl halides with alkylaluminum reagents (alkyl–alkyl Negishi coupling) is developed using an iron/bisphosphine catalyst system. The reaction shows high functional group tolerance: various primary alkyl halides possessing a non-protected indole, carboxyl, or hydroxy group are coupled with primary alkylaluminum reagents in good yields. Potassium fluoride plays a key role to promote the reaction by generating an aluminate species, which facilitates the transmetalation between the organoaluminum and the iron catalyst.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.180954