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过渡金属催化的酚类和芳基硫醇的合成。

Transition-metal-catalyzed synthesis of phenols and aryl thiols.

作者信息

Liu Yajun, Liu Shasha, Xiao Yan

机构信息

College of Life Science and Medicine, Dalian University of Technology, Panjin 124221, China.

Department of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China.

出版信息

Beilstein J Org Chem. 2017 Mar 23;13:589-611. doi: 10.3762/bjoc.13.58. eCollection 2017.

DOI:10.3762/bjoc.13.58
PMID:28405239
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5372758/
Abstract

Phenols and aryl thiols are fundamental building blocks in organic synthesis and final products with interesting biological activities. Over the past decades, substantial progress has been made in transition-metal-catalyzed coupling reactions, which resulted in the emergence of new methods for the synthesis of phenols and aryl thiols. Aryl halides have been extensively studied as substrates for the synthesis of phenols and aryl thiols. In very recent years, C-H activation represents a powerful strategy for the construction of functionalized phenols directly from various arenes. However, the synthesis of aryl thiols through C-H activation has not been reported. In this review, a brief overview is given of the recent advances in synthetic strategies for both phenols and aryl thiols.

摘要

酚类和芳基硫醇是有机合成中的基本结构单元,也是具有有趣生物活性的最终产物。在过去几十年中,过渡金属催化的偶联反应取得了重大进展,这导致了合成酚类和芳基硫醇的新方法的出现。芳基卤化物作为合成酚类和芳基硫醇的底物已得到广泛研究。近年来,C-H活化是一种直接从各种芳烃构建官能化酚类的强大策略。然而,尚未有通过C-H活化合成芳基硫醇的报道。在本综述中,简要概述了酚类和芳基硫醇合成策略的最新进展。

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Recent Advances in First-Row Transition Metal-Catalyzed Reductive Coupling Reactions for π-Bond Functionalization and C-Glycosylation.用于π键官能化和C-糖基化的第一行过渡金属催化还原偶联反应的最新进展
Acc Chem Res. 2023 Nov 21;56(22):3292-3312. doi: 10.1021/acs.accounts.3c00531. Epub 2023 Nov 2.
10
Advances in Rhodium-Catalyzed Oxidative Arene Alkenylation.铑催化氧化芳烃烯基化反应的研究进展
Acc Chem Res. 2020 Apr 21;53(4):920-936. doi: 10.1021/acs.accounts.0c00036. Epub 2020 Apr 2.

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Direct C-H Hydroxylation of -Heteroarenes and Benzenes Base-Catalyzed Halogen Transfer.含杂芳烃和苯的直接C-H羟基化反应 碱催化的卤素转移反应
J Am Chem Soc. 2024 Apr 10;146(14):9755-9767. doi: 10.1021/jacs.3c14058. Epub 2024 Mar 26.
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Direct conversion of carboxylic acids to free thiols radical relay acridine photocatalysis enabled by N-O bond cleavage.通过N-O键断裂实现的自由基接力吖啶光催化将羧酸直接转化为游离硫醇
Chem Sci. 2023 Dec 5;15(2):644-650. doi: 10.1039/d3sc05513b. eCollection 2024 Jan 3.
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Ligand-Enabled C-H Hydroxylation with Aqueous HO at Room Temperature.

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Directing group assisted -hydroxylation by C-H activation.导向基团辅助的C-H活化羟基化反应
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A diversity-oriented synthesis of bioactive benzanilides a regioselective C(sp)-H hydroxylation strategy.一种以多样性为导向的生物活性苯甲酰苯胺的合成——一种区域选择性C(sp)-H羟基化策略。
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Synthesis of 2,2'-biphenols through direct C(sp(2))-H hydroxylation of [1,1'-biphenyl]-2-ols.
在室温下用水相 HO 进行配体促进的 C-H 羟化反应。
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Selective hydroxylation of aryl iodides to produce phenols under mild conditions using a supported copper catalyst.使用负载型铜催化剂在温和条件下将芳基碘选择性羟基化以制备酚类。
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Catalytic synthesis of phenols with nitrous oxide.用一氧化二氮催化合成酚类。
Nature. 2022 Apr;604(7907):677-683. doi: 10.1038/s41586-022-04516-4. Epub 2022 Apr 27.
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Novel library synthesis of 3,4-disubstituted pyridin-2(1)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature.在室温离子氢化条件下通过吡啶 -2-氧基 -7-氮杂苯并三唑醚的裂解合成 3,4-二取代吡啶 -2(1)-酮的新型文库。
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Metal-free C-H mercaptalization of benzothiazoles and benzoxazoles using 1,3-propanedithiol as thiol source.以1,3 - 丙二硫醇作为硫醇源的苯并噻唑和苯并恶唑的无金属C-H硫缩醛化反应
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Investigations on Gold-Catalyzed Thioalkyne Activation Toward Facile Synthesis of Ketene Dithioacetals.关于金催化硫代炔烃活化用于简便合成乙烯酮二硫代缩醛的研究。
Chemistry. 2017 Aug 4;23(44):10506-10510. doi: 10.1002/chem.201702710. Epub 2017 Jul 20.
通过[1,1'-联苯]-2-醇的直接C(sp(2))-H羟基化合成2,2'-联苯酚
Chem Commun (Camb). 2016 Aug 18;52(69):10529-32. doi: 10.1039/c6cc04756d.
4
Preparation of tetrasubstituted pyrimido[4,5-]pyrimidine diones.四取代嘧啶并[4,5 - ]嘧啶二酮的制备。
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Copper-Catalyzed Reaction Cascade of Thiophenol Hydroxylation and S-Arylation through Disulfide-Directed C-H Activation.通过二硫化物导向的C-H活化实现铜催化的苯硫酚羟基化和S-芳基化反应级联
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6
Ligand-Enabled, Copper-Promoted Regio- and Chemoselective Hydroxylation of Arenes, Aryl Halides, and Aryl Methyl Ethers.配体促进、铜催化的芳烃、芳基卤化物和芳基甲基醚的区域和化学选择性羟基化反应
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7
Ru(II)-Catalyzed Site-Selective Hydroxylation of Flavone and Chromone Derivatives: The Importance of the 5-Hydroxyl Motif for the Inhibition of Aurora Kinases.钌(II)催化的黄酮和色酮衍生物的位点选择性羟化:5-羟基基序对抑制 Aurora 激酶的重要性。
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8
Cross-dehydrogenative coupling for the intermolecular C-O bond formation.交叉脱氢偶联反应在分子间 C-O 键形成中的应用。
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9
Palladium-Catalyzed Aryl C(sp(2))-H Bond Hydroxylation of 2-Arylpyridine Using TBHP as Oxidant.以叔丁基过氧化氢为氧化剂,钯催化2-芳基吡啶的芳基C(sp(2))-H键羟基化反应
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10
Palladium catalyzed Csp2-H activation for direct aryl hydroxylation: the unprecedented role of 1,4-dioxane as a source of hydroxyl radicals.钯催化的Csp2-H活化用于直接芳基羟基化:1,4-二氧六环作为羟基自由基来源的前所未有的作用。
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