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首页> 外文期刊>Chemistry: A European journal >Transition-Metal-Free Formal Sonogashira Coupling and alpha-Carbonyl Arylation Reactions
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Transition-Metal-Free Formal Sonogashira Coupling and alpha-Carbonyl Arylation Reactions

机译：无过渡金属的形式Sonogashira偶联和α-碳酰化反应

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摘要

Transition-metal-free formal Sonogashira coupling and alpha-carbonyl arylation reactions have been developed. These transformations are based on the nucleophilic aromatic substitution (SNAr) of beta-carbonyl sulfones to electron-deficient aryl fluorides, producing a key intermediate that, depending on the reaction conditions, gives the aromatic alkynes or alpha-aryl carbonyl compounds. The development of these reactions is presented and, based on investigations under basic and acidic conditions, mechanisms have been proposed. To develop the formal Sonogashira coupling further, a milder, two-step protocol is also disclosed that expands the reaction concept. The scope of these reactions is demonstrated for the synthesis of Sonogashira and alpha-carbonyl arylated products from a range of electron-deficient aryl fluorides with a variety of functional groups and aryl-, heteroaryl-, alkyl-, and alkoxy-substituted sulfone nucleophiles. These transition-metal-free reactions complement the metal-catalyzed versions in terms of substitution patterns, simplicity, and reaction conditions.
机译：已开发出无过渡金属的形式化Sonogashira偶联和α-羰基芳基化反应。这些转化是基于β-羰基砜向电子缺陷型芳基氟化物的亲核芳族取代（SNAr），产生了关键中间体，根据反应条件，该中间体会生成芳族炔烃或α-芳基羰基化合物。介绍了这些反应的进展，并基于在碱性和酸性条件下的研究提出了机理。为了进一步开发正式的Sonogashira偶联，还公开了一种温和的两步方案，扩展了反应概念。证明了这些反应的范围可用于从一系列具有各种官能团的缺电子的芳基氟化物和芳基，杂芳基，烷基和烷氧基取代的砜亲核试剂合成Sonogashira和α-羰基芳基化产物。这些无过渡金属的反应在取代方式，简单性和反应条件方面与金属催化的反应形式互补。

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