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1.1.7 Gold/Gold Dual Catalysis 1.1.7金/金双催化
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00067
A. Hashmi
This chapter summarizes the reactions that have been reported that are based on dual gold catalysis. The chemistry typically involves diyne substrates, and leads to a broad range of carbo- and heterocycles. The literature up to 2019 is covered.
本章总结了已报道的基于双金催化的反应。该化学反应通常涉及二炔底物,并导致广泛的碳环和杂环。涵盖截至2019年的文献。
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引用次数: 0
1.1.6 Gold Dual Catalysis with Palladium, Nickel, or Rhodium 1.1.6金与钯、镍或铑的双重催化
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00061
N. Patil, A. G. Tathe, V. W. Bhoyare
The unique intermediates accessible by exploiting the soft π-acid character of gold catalysts, make them an attractive option for dual metal catalysis reactions. Together with palladium, nickel, or rhodium, each having their own distinct character, dual catalysis with gold offers exclusive opportunities for reactivity and selectivity in installing carbon–carbon and carbon–heteroatom linkages. For instance, gold dual catalysis with palladium can be an advanced tool for cross-coupling reactions. On the other hand, unlike palladium, nickel is more readily susceptible to single-electron redox processes and hence can offer reactivity both parallel to and different from that of palladium. Another potential candidate, rhodium, is considered for dual catalysis with gold because it showcases unique reactivity such as C–H activation/transmetalation and conjugate addition. When compared to using single-metal catalyst systems, such dual-metal associations result in efficient one-pot approaches to highly regio- and stereoselective syntheses of molecules via cross couplings, cycloadditions, or rearrangements.
利用金催化剂的软π酸性质可获得的独特中间体,使其成为双金属催化反应的有吸引力的选择。与钯、镍或铑一起,每一种都有自己独特的特征,与金的双重催化在安装碳-碳和碳杂原子键方面提供了独特的反应性和选择性。例如,金与钯的双重催化可以成为交叉偶联反应的先进工具。另一方面,与钯不同,镍更容易受到单电子氧化还原过程的影响,因此可以提供与钯相似或不同的反应性。另一个潜在的候选者,铑,被认为是与金的双重催化,因为它显示出独特的反应性,如C-H活化/金属转化和共轭加成。与使用单金属催化剂系统相比,这种双金属结合导致通过交叉偶联、环加成或重排高效的一锅方法来合成高度区域和立体选择性的分子。
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引用次数: 1
Back Matter 回到问题
Pub Date : 2020-01-01 DOI: 10.1055/b-0039-173190
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引用次数: 0
1.2.4 Gold/Photocatalyst Dual Catalysis 1.2.4金/光催化剂双催化
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00189
L. Barriault, M. Zidan, S. Rohe
The use of gold catalysts in classical two-electron cross-couplings is notoriously impractical due to the high oxidation potential of gold(I)/gold(III) [e.g., E0 (AuI/AuIII) = +1.36 V]. However, when used in tandem with photocatalysts, the gold center can be oxidized one electron at a time, making cross-coupling style reactions with gold more viable. The gold(III) intermediate also has the potential to act as a Lewis acid prior to its reductive elimination step, which has spurred development of multi-bond-forming dual catalytic transformations. This dual-catalytic strategy is also applied in reactions with gold as a photocatalyst in conjunction with an organocatalyst to effectuate traditionally challenging cross couplings.
众所周知,在经典的双电子交叉耦合中使用金催化剂是不切实际的,因为金(I)/金(III)的氧化电位很高[例如,E0 (AuI/AuIII) = +1.36 V]。然而,当与光催化剂串联使用时,金中心可以一次氧化一个电子,使与金的交叉偶联反应更可行。金(III)中间体在其还原消除步骤之前也具有作为路易斯酸的潜力,这促进了多键形成双催化转化的发展。这种双催化策略也应用于光催化剂与有机催化剂的反应中,以实现传统上具有挑战性的交叉偶联。
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引用次数: 0
1.1.4 Iridium/Zinc and Iridium/Copper Dual Catalysis 1.1.4铱/锌和铱/铜双催化
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00041
X. Huo, R. He, W. Zhang
Synergistic bimetallic catalysis is gaining increasing attention due to its advantages over traditional catalytic methodologies. These advantages include double activation, accurate control of reaction sites, double stereochemical control, and potential in stereodivergent synthesis. This review documents advances in the field and provides an up-to-date overview of recent developments in the use of iridium/zinc and iridium/copper catalyst systems.
协同双金属催化由于其优于传统催化方法的优点而受到越来越多的关注。这些优点包括双重活化、精确控制反应位点、双重立体化学控制和立体发散合成的潜力。本文综述了该领域的进展,并提供了铱/锌和铱/铜催化剂系统使用的最新发展概况。
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引用次数: 0
1.1.3 Rhodium/Palladium Dual Catalysis 1.1.3铑/钯双催化
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00029
U. Kim, S.-g. Lee
This chapter reviews the development and applications of rhodium/palladium dual catalysis in organic synthesis. Dual catalysis can be broadly classified into two types: (1) Synergistic dual catalysis, where two independent rhodium and palladium catalytic cycles operate simultaneously to activate two different starting materials with balanced kinetics to afford two catalytically activated intermediates. These activated intermediates react with each other to afford the final product. (2) Orthogonal tandem dual catalysis, where two catalytic cycles operate in a sequential manner, one after the other, to promote two or more mechanistically distinct reaction steps in a single pot to furnish the product. The first part of the chapter covers synergistic rhodium/palladium dual catalysis, detailing examples that feature a direct reaction between rhodium-activated intermediates and orthogonal, palladium-activated intermediates. The second part of the chapter describes one-pot reactions that utilize initial rhodium catalysis and sequential palladium catalysis. A single example where initial palladium catalysis is followed by subsequent rhodium catalysis is also presented.
本章综述了铑/钯双催化在有机合成中的研究进展及其应用。双催化大致可分为两种类型:(1)协同双催化,即两个独立的铑和钯催化循环同时运行,激活两种不同的起始材料,动力学平衡,提供两种催化活化的中间体。这些活化的中间体相互反应产生最终产物。(2)正交串联双催化,其中两个催化循环以顺序的方式进行,一个接一个,在一个锅中促进两个或多个机械上不同的反应步骤,以提供产品。本章的第一部分介绍了协同铑/钯双催化,详细介绍了铑活化中间体和正交钯活化中间体之间直接反应的例子。本章的第二部分描述了利用初始铑催化和顺序钯催化的一锅反应。一个单一的例子,其中最初的钯催化后,随后的铑催化也提出。
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引用次数: 0
1.1.1 General Principles of Metal/Metal Dual Catalysis 1.1.1金属/金属双催化一般原理
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00002
Y. Nakao
The background and principles of dual metal/metal catalysis are briefly introduced in this section, with a particular focus on novel C–C bond-forming cross-coupling-type reactions. By taking advantage of synergistic dual metal/metal catalysis, these transformations have provided the synthetic and organometallic communities with new ideas to design challenging transformations that are difficult to catalyze using a conventional, single metal catalyst.
本节简要介绍了双金属/金属催化的背景和原理,重点介绍了新型的C-C键形成交叉偶联型反应。通过利用协同双金属/金属催化,这些转化为合成和有机金属社区提供了新的思路,以设计难以使用传统的单金属催化剂催化的具有挑战性的转化。
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引用次数: 0
1.2.3 Palladium/Photocatalyst Dual Catalysis 1.2.3钯/光催化剂双催化
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00168
K. Muralirajan, M. Rueping
Palladium-catalyzed cross-coupling reactions are of great importance in chemistry. Merging palladium catalysis with photoredox catalysis has recently led to promising improvements, and typical problems associated with the use of stoichiometric oxidants, higher temperature, and harsh reaction conditions could be addressed. This chapter outlines recent developments in palladium/photoredox dual catalyzed C–C and C–N bond-formation reactions using visible-light irradiation.
钯催化的交叉偶联反应在化学中具有重要意义。钯催化和光氧化还原催化的合并最近带来了有希望的改进,并且可以解决与使用化学计量氧化剂,更高温度和恶劣反应条件相关的典型问题。本章概述了可见光照射下钯/光氧化还原双催化C-C和C-N键形成反应的最新进展。
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引用次数: 0
1.2.2 Nickel/Photocatalyst Dual Catalysis 1.2.2镍/光催化剂双催化
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00100
D. Primer, G. Molander
This chapter outlines the broad scope of photoredox/nickel dual catalysis. Among the newer approaches to organic synthesis that engender the concept of dual catalysis, photoredox/nickel dual-catalytic cross-coupling reactions comprise one of the most rapidly developing and powerful tactics. Taken as a whole, these transformations enable novel carbon–carbon and carbon–heteroatom bond constructions that were previously challenging, if not impossible, to carry out. Most remarkably, these processes are most often carried out under near-neutral reaction conditions at ambient temperatures, with the energy to drive the reactions being provided solely by visible-light sources, thus enabling the incorporation of a broad range of diverse functional groups. As described, the development of these processes therefore provides one means to address the longstanding challenge of late-stage assembly of highly functionalized molecules via cross-coupling strategies.
本章概述了光氧化还原/镍双催化的广泛范围。在产生双催化概念的有机合成新方法中,光氧化还原/镍双催化交叉偶联反应是发展最快和最强大的策略之一。作为一个整体,这些转变使新的碳-碳和碳杂原子键结构成为可能,这在以前是具有挑战性的,如果不是不可能的话。最值得注意的是,这些过程通常是在环境温度下的近中性反应条件下进行的,驱动反应的能量仅由可见光源提供,因此可以结合广泛的不同官能团。如上所述,这些过程的发展因此提供了一种方法来解决通过交叉耦合策略进行高功能化分子后期组装的长期挑战。
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引用次数: 0
1.1.5 Gold/Iron Dual Catalysis 1.1.5金/铁双催化
Pub Date : 2020-01-01 DOI: 10.1055/sos-sd-231-00054
X. Shi, J. Wang
Dual gold/iron catalysis has emerged in the past decade as a fast, efficient and economical method to access molecular complexity. Preliminary results are reviewed herein.
金/铁双催化是近十年来出现的一种快速、高效、经济的研究分子复杂性的方法。本文回顾了初步结果。
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引用次数: 0
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Dual Catalysis in Organic Synthesis 1
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