Synthesis ( IF 2.2 ) Pub Date : 2018-10-29 , DOI: 10.1055/s-0037-1611064 Miriam L O'Duill 1, 2 , Keary M Engle 2
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Abstract
Protodepalladation is the redox-neutral conversion of a C–Pd(II) bond into a C–H bond via reaction with a Brønsted acid. It is the microscopic reverse of Pd(II)-mediated C–H cleavage. In the context of catalytic reaction development, protodepalladation offers a means of converting organopalladium(II) intermediates into organic products without a change in oxidation state at the metal center. Hence, when integrated into catalytic cycles, it can be a uniquely enabling elementary step. The goal of this review is to provide an overview of protodepalladation, including exploration of different reaction types, discussion of literature examples, and analysis of mechanistic features. Our hope is that this review will stimulate other researchers in the field to pursue new applications of this underexploited step in catalysis.
1 Introduction
2 Mechanistic Considerations
3 Examples of Synthetically Enabling Protodepalladation Reactions
3.1 Alkenylpalladium Species
3.2 Arylpalladium Species
3.3 Palladium Enolates
3.4 Alkylpalladium Species
4 Conclusion
Protodepalladation is the redox-neutral conversion of a C–Pd(II) bond into a C–H bond via reaction with a Brønsted acid. It is the microscopic reverse of Pd(II)-mediated C–H cleavage. In the context of catalytic reaction development, protodepalladation offers a means of converting organopalladium(II) intermediates into organic products without a change in oxidation state at the metal center. Hence, when integrated into catalytic cycles, it can be a uniquely enabling elementary step. The goal of this review is to provide an overview of protodepalladation, including exploration of different reaction types, discussion of literature examples, and analysis of mechanistic features. Our hope is that this review will stimulate other researchers in the field to pursue new applications of this underexploited step in catalysis.
1 Introduction
2 Mechanistic Considerations
3 Examples of Synthetically Enabling Protodepalladation Reactions
3.1 Alkenylpalladium Species
3.2 Arylpalladium Species
3.3 Palladium Enolates
3.4 Alkylpalladium Species
4 Conclusion
中文翻译：
原型脱钯作为催化的战略性基本步骤
抽象的
原型脱钯是通过与布朗斯台德酸反应，将 C-Pd(II) 键氧化还原中性转化为 C-H 键。它是 Pd(II) 介导的 C-H 裂解的微观逆转。在催化反应开发的背景下，原脱钯提供了一种将有机钯(II)中间体转化为有机产物而不改变金属中心氧化态的方法。因此，当集成到催化循环中时，它可以成为一个独特的基本步骤。本综述的目的是提供原型脱钯的概述，包括对不同反应类型的探索、文献实例的讨论以及机械特征的分析。我们希望这篇综述能够刺激该领域的其他研究人员探索这一尚未充分开发的催化步骤的新应用。
1 简介
2 机械方面的考虑
3 合成原型脱钯反应的例子
3.1 烯基钯种类
3.2 芳基钯种类
3.3 烯醇化钯
3.4 烷基钯种类
4 结论
原型脱钯是通过与布朗斯台德酸反应，将 C-Pd(II) 键氧化还原中性转化为 C-H 键。它是 Pd(II) 介导的 C-H 裂解的微观逆转。在催化反应开发的背景下，原脱钯提供了一种将有机钯(II)中间体转化为有机产物而不改变金属中心氧化态的方法。因此，当集成到催化循环中时，它可以成为一个独特的基本步骤。本综述的目的是提供原型脱钯的概述，包括对不同反应类型的探索、文献实例的讨论以及机械特征的分析。我们希望这篇综述能够刺激该领域的其他研究人员探索这一尚未充分开发的催化步骤的新应用。
1 简介
2 机械方面的考虑
3 合成原型脱钯反应的例子
3.1 烯基钯种类
3.2 芳基钯种类
3.3 烯醇化钯
3.4 烷基钯种类
4 结论
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