Issue 18, 2024
From the journal:

RSC Advances

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

Zheng-Ying Wang,a   Shi-Zheng Liu,a   Cong Guo,a   Yi-Zheng Cheng,a   Qiang Li, ORCID logo *a   Jianmin Dou*a  and  Dacheng Li*a  

* Corresponding authors

a Shandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252000, P. R. China
E-mail: liqiang9@lcu.edu.cn, jmdou@lcu.edu.cn, lidacheng62@163.com

Abstract

A novel method was developed for synthesizing γ-alkyl ketones via 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 via halide exchange, thus avoiding the formation of alkyl dimers. This reaction possessed excellent regioselectivity and high step economy circumventing in situ or pregenerated organometallics.

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

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Article information

DOI
https://doi.org/10.1039/D4RA02616K
Article type
Paper
Submitted
07 Apr 2024
Accepted
15 Apr 2024
First published
22 Apr 2024
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2024,14, 12883-12887

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

Z. Wang, S. Liu, C. Guo, Y. Cheng, Q. Li, J. Dou and D. Li, RSC Adv., 2024, 14, 12883 DOI: 10.1039/D4RA02616K

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