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α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions
Current Organic Chemistry ( IF 1.7 ) Pub Date : 2019-06-30 , DOI: 10.2174/1385272823666190926092242
Humaira Y. Gondal 1 , Zain M. Cheema 1 , Abdul R. Raza 1 , Ahmed Abbaskhan 2 , M. I. Chaudhary 2
Affiliation  

Following numerous applications of Wittig reaction now functionalized phosphonium salts are gaining attention due to their characteristic properties and diverse reactivity. This review is focused on α-alkoxyalkyl triphenylphosphonium salts: an important class of functionalized phosphonium salts. Alkoxymethyltriphenylphosphonium salts are majorly employed in the carbon homologation of carbonyl compounds and preparation of enol ethers. Their methylene insertion strategy is extensively demonstrated in the total synthesis of a wide range of natural products and other important organic molecules. Similarly enol ethers prepared thereof are important precursors for different organic transformations like Diels-Alder reaction, Claisen rearrangement, Coupling reactions, Olefin metathesis and Nazarov cyclization. Reactivity of these α-alkoxyalkylphosphonium salts have also been studied in the nucleophilic substitution reactions. A distinctive application of this class of phosphonium salts was recently reported in the phenylation of carbonyl compounds under very mild conditions. Synthesis of structurally diverse alkoxymethyltriphenylphosphonium salts with variation in alkoxy groups as well as counter anions are reported in literature. Here we present a detailed account of different synthetic methodologies for the preparation of this unique class of quaternary phosphonium salts and their applications in organic synthesis.



中文翻译:

α-烷氧基烷基三苯基phosph盐:合成与反应

在Wittig反应的众多应用之后,由于它们的特性和多样的反应性,现在官能化的salts盐正受到关注。本文的重点是α-烷氧基烷基三苯基phosph盐:一类重要的官能化phospho盐。烷氧基甲基三苯基phosph盐主要用于羰基化合物的碳均化和烯醇醚的制备中。它们的亚甲基插入策略在各种天然产物和其他重要有机分子的全合成中得到了充分证明。类似地,由其制备的烯醇醚是用于不同有机转化如Diels-Alder反应,Claisen重排,偶联反应,烯烃复分解和Nazarov环化的重要前体。这些α-烷氧基烷基phosph盐的反应性也已经在亲核取代反应中进行了研究。最近报道了这类of盐的独特应用是在非常温和的条件下羰基化合物的苯基化。文献报道了具有烷氧基和抗衡阴离子变化的结构多样的烷氧基甲基三苯基phosph盐的合成。在这里,我们介绍了用于制备这种独特的季phospho盐类及其在有机合成中的应用的不同合成方法的详细说明。文献报道了具有烷氧基和抗衡阴离子变化的结构多样的烷氧基甲基三苯基phosph盐的合成。在这里,我们介绍了用于制备这种独特的季phospho盐类及其在有机合成中的应用的不同合成方法的详细说明。文献报道了具有烷氧基和抗衡阴离子变化的结构多样的烷氧基甲基三苯基phosph盐的合成。在这里,我们介绍了用于制备这种独特的季phospho盐类及其在有机合成中的应用的不同合成方法的详细说明。

更新日期:2019-06-30
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