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镍催化1,3-丁二烯的四组分羰基化反应合成β,γ-不饱和酮

Nickel-Catalyzed Four-Component Carbonylation of 1,3-Butadiene To Access β,γ-Unsaturated Ketones.

作者信息

Teng Bing-Hong, Bao Zhi-Peng, Zhao Yingying, Wu Xiao-Feng

机构信息

Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China.

School of Chemistry and Chemical Engineering, Liaoning Normal University, 850 Huanghe Road, Dalian 116029, China.

出版信息

Org Lett. 2024 Jun 7;26(22):4779-4783. doi: 10.1021/acs.orglett.4c01599. Epub 2024 May 28.

Abstract

A new strategy to obtain β,γ-unsaturated ketones via the cross-coupling of 1,3-butadiene, alkyl bromides, and arylboronic acids under 1 bar of CO with nickel as the catalyst has been developed. This newly developed four-component carbonylation procedure features advantages including using a cheap catalytic system, high step economy, mild reaction conditions, and excellent 1,4-regioselectivity, thereby providing a sustainable and alternative tool for β,γ-unsaturated ketones production compared to the present tactics. To elucidate the application potential of this method, olefin synthons are derived from the representative coupling product.

摘要

已开发出一种新策略,在1巴CO压力下,以镍为催化剂,通过1,3 - 丁二烯、烷基溴和芳基硼酸的交叉偶联反应来制备β,γ - 不饱和酮。这种新开发的四组分羰基化方法具有诸多优点,包括使用廉价的催化体系、高原子经济性、温和的反应条件以及出色的1,4 - 区域选择性,因此与现有策略相比,为β,γ - 不饱和酮的生产提供了一种可持续的替代方法。为阐明该方法的应用潜力,从代表性偶联产物衍生出烯烃合成子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/653e/11165585/1195b9563810/ol4c01599_0001.jpg

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