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过渡金属和稀土金属催化下吡啶C(sp) -H键的官能团化

Pyridine C(sp)-H bond functionalization under transition-metal and rare earth metal catalysis.

作者信息

Sindhe Haritha, Reddy Malladi Mounika, Rajkumar Karthikeyan, Kamble Akshay, Singh Amardeep, Kumar Anand, Sharma Satyasheel

机构信息

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research - Ahmedabad, Gandhinagar, Gujarat, 382355, India.

Department of Natural Products, National Institute of Pharmaceutical Education and Research - Ahmedabad, Gandhinagar, Gujarat, 382355, India.

出版信息

Beilstein J Org Chem. 2023 Jun 12;19:820-863. doi: 10.3762/bjoc.19.62. eCollection 2023.

DOI:10.3762/bjoc.19.62
PMID:37346497
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10280098/
Abstract

Pyridine is a crucial heterocyclic scaffold that is widely found in organic chemistry, medicines, natural products, and functional materials. In spite of the discovery of several methods for the synthesis of functionalized pyridines or their integration into an organic molecule, new methodologies for the direct functionalization of pyridine scaffolds have been developed during the past two decades. In addition, transition-metal-catalyzed C-H functionalization and rare earth metal-catalyzed reactions have flourished over the past two decades in the development of functionalized organic molecules of concern. In this review, we discuss recent achievements in the transition-metal and rare earth metal-catalyzed C-H bond functionalization of pyridine and look into the mechanisms involved.

摘要

吡啶是一种至关重要的杂环骨架,广泛存在于有机化学、药物、天然产物和功能材料中。尽管已发现多种合成功能化吡啶或将其整合到有机分子中的方法,但在过去二十年中仍开发出了吡啶骨架直接功能化的新方法。此外,在过去二十年中,过渡金属催化的C-H官能化和稀土金属催化的反应在相关功能化有机分子的开发中蓬勃发展。在本综述中,我们讨论了过渡金属和稀土金属催化的吡啶C-H键官能化的最新成果,并探究其中涉及的机理。

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6
A review on the assembly of multi-substituted pyridines Co-catalyzed [2 + 2 + 2] cycloaddition with nitriles.多取代吡啶的组装:腈协同[2+2+2]环加成反应的研究综述。
Org Biomol Chem. 2022 Sep 28;20(37):7391-7404. doi: 10.1039/d2ob01344d.
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Transition-metal-catalyzed C-H bond alkylation using olefins: recent advances and mechanistic aspects.过渡金属催化烯烃的 C-H 键烷基化反应:最新进展和反应机理方面。
Chem Soc Rev. 2022 Aug 30;51(17):7358-7426. doi: 10.1039/d1cs00923k.
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Enantio- and Regioselective Ni-Catalyzed -C-H Alkylation of Pyridines with Styrenes via Intermolecular Hydroarylation.对映选择性和区域选择性镍催化吡啶与苯乙烯的间 C-H 烷基化反应通过分子间氢芳基化反应。
J Am Chem Soc. 2022 Aug 3;144(30):13643-13651. doi: 10.1021/jacs.2c04043. Epub 2022 Jul 20.
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Advancements in Visible-Light-Enabled Radical C(sp)2-H Alkylation of (Hetero)arenes.可见光促进的(杂)芳烃C(sp)2-H自由基烷基化反应的进展
Synthesis (Stuttg). 2019 Mar;51(5):1063-1072. doi: 10.1055/s-0037-1611658. Epub 2019 Jan 25.
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Alkyl/Glycosyl Sulfoxides as Radical Precursors and Their Use in the Synthesis of Pyridine Derivatives.烷基/糖苷砜作为自由基前体及其在吡啶衍生物合成中的应用。
Angew Chem Int Ed Engl. 2022 Aug 1;61(31):e202204922. doi: 10.1002/anie.202204922. Epub 2022 Jun 23.