α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions

Author(s): Humaira Y. Gondal*, Zain M. Cheema, Abdul R. Raza, Ahmed Abbaskhan, M. I. Chaudhary.

Journal Name: Current Organic Chemistry

Volume 23 , Issue 16 , 2019

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Graphical Abstract:


Abstract:

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.

Keywords: Quaternary phosphonium salts, functionalized phosphonium salts, methoxymethyl triphenylphosphonium chloride, carbon homologation, vinyl ethers, enol ethers, nucleophilic phenylation.

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