From Pyridine-N-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy

2021 ◽  
Author(s):  
Dmitry I. Bugaenko ◽  
Marina A. Yurovskaya ◽  
Alexander V. Karchava
Keyword(s):  
Phosphonium Salts

α-Alkoxyalkyl Triphenylphosphonium Salts: Synthesis and Reactions

2019 ◽  
Vol 23 (16) ◽  
pp. 1738-1755
Author(s):  
Humaira Y. Gondal ◽  
Zain M. Cheema ◽  
Abdul R. Raza ◽  
Ahmed Abbaskhan ◽  
M. I. Chaudhary
Keyword(s):  
Carbonyl Compounds ◽  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Coupling Reactions ◽  
Phosphonium Salts ◽  
Organic Transformations ◽  
Enol Ethers ◽  
Wide Range ◽  
Synthetic Methodologies ◽  
Alkoxy Groups

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.

Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts

2021 ◽  
Author(s):  
Meghan Fragis ◽  
Jackson L. Deobald ◽  
Srinivas Dharavath ◽  
Jeffrey Scott ◽  
Jakob Magolan
Keyword(s):  
Phosphonium Salts

Unusual Application for Phosphonium Salts and Phosphoranes: Synthesis of Chalcogenides

2021 ◽  
Author(s):  
Igor M. R. Moura ◽  
Arisson Tranquilino ◽  
Barbara G. Sátiro ◽  
Ricardo O. Silva ◽  
Diogo de Oliveira-Silva ◽  
...  
Keyword(s):  
Phosphonium Salts

The Study of the Conformation and Dynamics of the New Quaternary Phosphonium Salts by NMR Spectroscopy

2014 ◽  
Vol 45 (7) ◽  
pp. 653-665 ◽  
Author(s):  
Oksana Aganova ◽  
Leisan Galiullina ◽  
Albert Aganov ◽  
Yurii Shtyrlin ◽  
Mikhail Pugachev ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Phosphonium Salts ◽  
Quaternary Phosphonium Salts

Phosphonium salts. III. The action of cyanide ion and other nucleophiles on some bis-phosphonium salts

1969 ◽  
Vol 22 (7) ◽  
pp. 1405 ◽  
Author(s):  
JJ Brophy ◽  
MJ Gallagher
Keyword(s):  
Sodium Azide ◽  
Sodium Methoxide ◽  
Sodium Acetate ◽  
Potassium Cyanide ◽  
Dimethyl Sulphoxide ◽  
High Yield ◽  
Phosphonium Salts ◽  
Elimination Reaction ◽  
Cyanide Ion ◽  
Reaction Proceeds

Cyclic and acyclic bis-phosphonium salts with a two-carbon bridge are smoothly cleaved to phosphines in high yield by potassium cyanide in dimethyl sulphoxide. Evidence is presented that the reaction proceeds by an elimination-addition sequence. An elimination reaction also occurs when sodium methoxide, sodium azide, sodium acetate, and triethylamine react with ethane-1,2-bis(tri-phenylphosphonium) dibromide. ��� In a novel reaction, triphenylphosphine is converted into its oxide by a mixture of sodium azide and dimethyl sulphoxide.

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