Nickel-catalyzed γ-alkylation of cyclopropyl ketones with unactivated primary alkyl chlorides: balancing reactivity and selectivity via halide exchange

A novel method was developed for synthesizing γ-alkyl ketones nickel-catalyzed cross-electrophile coupling of cyclopropyl ketones and non-activated primary alkyl chlorides. High reactivity and selectivity can be achieved with sodium iodide as a crucial cocatalyst that generates a low concentration o...

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Bibliographic Details
Published inRSC advances Vol. 14; no. 18; pp. 12883 - 12887
Main Authors Wang, Zheng-Ying, Liu, Shi-Zheng, Guo, Cong, Cheng, Yi-Zheng, Li, Qiang, Dou, Jianmin, Li, Dacheng
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 16.04.2024
The Royal Society of Chemistry
Subjects
Alkylation
Chemical synthesis
Chemistry
Chlorides
Ketones
Nickel
Organometallic compounds
Regioselectivity
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Summary:A novel method was developed for synthesizing γ-alkyl ketones nickel-catalyzed cross-electrophile coupling of cyclopropyl ketones and non-activated primary alkyl chlorides. High reactivity and selectivity can be achieved with sodium iodide as a crucial cocatalyst that generates a low concentration of alkyl iodide halide exchange, thus avoiding the formation of alkyl dimers. This reaction possessed excellent regioselectivity and high step economy circumventing or pregenerated organometallics.
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ISSN:2046-2069
2046-2069
DOI:10.1039/d4ra02616k