与镍、可见光和介孔氮化石墨碳的 C(sp2)-S 交叉偶联反应

IF 9.2 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Green Chemistry Pub Date : 2024-05-20 DOI:10.1039/d3gc04517j
Maksim Nikitin , Florence Babawale , Sena Tastekin , Markus Antonietti , Indrajit Ghosh , Burkhard König
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引用次数: 0

摘要

交叉偶联反应在现代有机合成中起着至关重要的作用,它可以构建合成转化所需的 C-C 或 C-(het)原子键。虽然 C(sp2)-C 和 C(sp2)-N 交叉偶联反应受到了广泛关注,但最近的研究进展也凸显了 C(sp2)-S 交叉偶联反应的重要性。通过这些反应可以合成药物和材料等有价值的化合物。在最近的一份报告中,我们介绍了自适应动态均相催化(AD-HoC)作为 C(sp2)-S 交叉偶联反应的一种高效方法。这种方法无需任何配体、碱或额外添加剂,只需依赖基本参数即可运行。在本报告中,我们讨论了介孔氮化石墨(mpg-CN)作为全有机异质光催化剂在此类转化中的应用。通过 50 个合成实例展示了该反应的多功能性和稳健性,收率高达 98%。此外,使用 mpg-CN 作为催化剂,还能轻松地从反应混合物中回收光催化剂,并能通过简单的设置,连续执行多个交叉偶联反应,获得一致的所需产物产率。这种方法在操作简便性和环境影响方面都是该领域的一大进步,而这正是我们所期望的可持续发展特性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

C(sp2)–S cross-coupling reactions with nickel, visible light, and mesoporous graphitic carbon nitride†

C(sp2)–S cross-coupling reactions with nickel, visible light, and mesoporous graphitic carbon nitride†

C(sp2)–S cross-coupling reactions with nickel, visible light, and mesoporous graphitic carbon nitride†

Cross-coupling reactions play a vital role in modern organic synthesis, enabling the construction of necessary C–C or C–(het)atom bonds for synthetic transformations. Although C(sp2)–C and C(sp2)–N cross-coupling reactions have received significant attention, recent advancements have also highlighted the significance of C(sp2)–S cross-coupling reactions. These reactions lead to the synthesis of valuable compounds, including pharmaceuticals and materials. In a recent report, we introduced Adaptive Dynamic Homogeneous Catalysis (AD-HoC) as an efficient method for C(sp2)–S cross-coupling reactions. This method operates without the need for any ligands, base, or additional additives, relying solely on essential parameters. In this report, we discuss the use of mesoporous graphitic carbon nitride (mpg-CN) as an all-organic heterogeneous photocatalyst in such transformations. The versatility and robustness of the reaction are showcased with fifty synthetic examples, achieving up to a 98% yield. The use of mpg-CN as a catalyst additionally enables the easy recovery of the photocatalyst from the reaction mixture and facilitates the sequential execution of multiple cross-coupling reactions with consistent yields of the desired products using a simple setup. This approach is a significant advancement in the field, both in terms of operational simplicity and environmental impact, traits that we all envision for sustainability.

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来源期刊
Green Chemistry
Green Chemistry 化学-化学综合
CiteScore
16.10
自引率
7.10%
发文量
677
审稿时长
1.4 months
期刊介绍: Green Chemistry is a journal that provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998), which defines green chemistry as the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry aims to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. The journal welcomes submissions on all aspects of research relating to this endeavor and publishes original and significant cutting-edge research that is likely to be of wide general appeal. For a work to be published, it must present a significant advance in green chemistry, including a comparison with existing methods and a demonstration of advantages over those methods.
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