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镍催化环丙基酮与未活化伯烷基氯的γ-烷基化反应：平衡反应活性和选择性——卤化物交换

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

作者信息

Wang Zheng-Ying, Liu Shi-Zheng, Guo Cong, Cheng Yi-Zheng, Li Qiang, Dou Jianmin, Li Dacheng

机构信息

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

出版信息

RSC Adv. 2024 Apr 22;14(18):12883-12887. doi: 10.1039/d4ra02616k. eCollection 2024 Apr 16.

DOI:10.1039/d4ra02616k
PMID:38650692
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11033608/
Abstract

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.

摘要

开发了一种合成γ-烷基酮的新方法，该方法是通过镍催化环丙基酮与未活化的伯烷基氯进行交叉亲电偶联反应。以碘化钠作为关键的助催化剂，通过卤化物交换生成低浓度的烷基碘，从而避免烷基二聚体的形成，可实现高反应活性和选择性。该反应具有优异的区域选择性和高原子经济性，避免了使用预生成的有机金属化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/d15f9720e59f/d4ra02616k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/5ddd07d50a9b/d4ra02616k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/daf903f6c306/d4ra02616k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/6b1b665f65b0/d4ra02616k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/d15f9720e59f/d4ra02616k-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/5ddd07d50a9b/d4ra02616k-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/daf903f6c306/d4ra02616k-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/6b1b665f65b0/d4ra02616k-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/44a0/11033608/d15f9720e59f/d4ra02616k-s4.jpg

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Nickel-catalyzed γ-alkylation of cyclopropyl ketones with unactivated primary alkyl chlorides: balancing reactivity and selectivity halide exchange.镍催化环丙基酮与未活化伯烷基氯的γ-烷基化反应：平衡反应活性和选择性——卤化物交换
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本文引用的文献

1
Ligand-Metal Cooperation Enables Net Ring-Opening C-C Activation / Difunctionalization of Cyclopropyl Ketones.配体-金属协同作用实现环丙基酮的净开环C-C活化/双官能化
ACS Catal. 2023 Sep 1;13(17):11277-11290. doi: 10.1021/acscatal.3c02643. Epub 2023 Aug 11.
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Nickel-Catalyzed C(sp)-Sb Coupling of Chlorostibines with Unactivated Alkyl Chlorides and In Vitro Anticancer Activity of Products.镍催化氯代锡与未活化的烷基氯的 C(sp)-Sb 偶联反应及产物的体外抗癌活性。
Org Lett. 2024 Jan 12;26(1):344-349. doi: 10.1021/acs.orglett.3c04008. Epub 2023 Dec 26.
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Transition-Metal-Catalyzed C-C Bond Formation from C-C Activation.
过渡金属催化的由碳-碳活化形成碳-碳键
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Photoinduced activation of alkyl chlorides.光致氯代烷烃的活化
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Metal-catalysed C-C bond formation at cyclopropanes.环丙烷上的金属催化碳-碳键形成
Nat Rev Chem. 2023 Aug;7(8):548-560. doi: 10.1038/s41570-023-00499-6. Epub 2023 May 22.
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Nickel-catalyzed reductive coupling of arylcarboxylic acid 2-pyridyl esters with alkyl methanesulfonates: access to alkyl aryl ketones.镍催化的芳基羧酸 2-吡啶酯与烷基甲磺酸盐的还原偶联：获得烷基芳基酮。
Org Biomol Chem. 2023 Apr 26;21(16):3423-3431. doi: 10.1039/d3ob00293d.
7
Iron-Catalyzed Reductive Ring Opening/-Difluoroallylation of Cyclopropyl Ketones.铁催化的环丙基酮的还原开环/二氟烯丙基化反应。
Org Lett. 2023 Mar 24;25(11):1883-1888. doi: 10.1021/acs.orglett.3c00398. Epub 2023 Mar 13.
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Nickel-Catalyzed Decarbonylative Reductive Alkylation of Aroyl Fluorides with Alkyl Bromides.镍催化芳酰氟与溴代烷烃的脱羰还原烷基化反应
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Mechanistic views and computational studies on transition-metal-catalyzed reductive coupling reactions.过渡金属催化的还原偶联反应的机理观点与计算研究
Chem Soc Rev. 2022 Dec 12;51(24):9986-10015. doi: 10.1039/d2cs00371f.
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Org Lett. 2022 Jun 10;24(22):3987-3992. doi: 10.1021/acs.orglett.2c01390. Epub 2022 May 31.