scholarly journals Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts

2021 ◽  
Author(s):  
Marion Till ◽  
Verena Streitferdt ◽  
Daniel J Scott ◽  
Michael Mende ◽  
Ruth M Gschwind ◽  
...  
Keyword(s):  
White Phosphorus ◽  
Photochemical Transformation ◽  
Phosphonium Salts ◽  
Elemental Phosphorus ◽  
Direct Arylation

Chlorobenzenes are important starting materials for the preparation of commercially valuable triarylphosphines and tetraarylphosphonium salts, but their use for the direct arylation of elemental phosphorus has been elusive. Here we...

scholarly journals Direct catalytic transformation of white phosphorus into arylphosphines and phosphonium salts

2019 ◽  
Vol 2 (12) ◽  
pp. 1101-1106 ◽  
Author(s):  
Ulrich Lennert ◽  
Percia Beatrice Arockiam ◽  
Verena Streitferdt ◽  
Daniel J. Scott ◽  
Christian Rödl ◽  
...  
Keyword(s):  
White Phosphorus ◽  
Catalytic Transformation ◽  
Phosphonium Salts

scholarly journals Catalytic Synthesis of Organophosphorus Compounds from Inorganic Derivatives of Low Valence Phosphorus

2016 ◽  
Vol 2 (1) ◽  
pp. 21 ◽  
Author(s):  
Gulshara S. Polimbetova ◽  
Rumiya R. Abdreimova ◽  
Farida Kh. Faisova
Keyword(s):  
Organophosphorus Compounds ◽  
Inorganic Compounds ◽  
Practical Importance ◽  
Catalytic Synthesis ◽  
White Phosphorus ◽  
Added Value ◽  
Sodium Hypophosphite ◽  
Organic Substrates ◽  
Phosphonium Salts ◽  
Derivatives Of

<p>A variety of new reactions of inorganic compounds of elemental and low valence phosphorus (phosphine, white phosphorus, sodium hypophosphite) with various organic substrates (alcohols, olefins, quinones) catalysed by different transition metal (Pd<sup>II</sup>, Hg<sup>II</sup>, Pt<sup>II</sup>, Pt<sup>IV</sup>, Ag<sup>I</sup>, Fe<sup>III</sup>, Cu<sup>II</sup>) salts leading to the formation of valuable organophosphorus derivatives (trialkylphosphates, dialkylphosphites, trialkylphoshinoxides, phosphonium salts) are reviewed. The principal features of the oxidative phosphorylation reactions which are of great practical importance are described. The mechanisms of the catalytic oxidative P-O and P-C coupling of phosphine, white phosphorus and hypophosphite with alcohols, olefins and quinones are considered. It has been shown that this catalytic protocol allows to provide a highly selective conversion of relatively inexpensive feedstocks to desirable higher added-value products.</p>

scholarly journals Black Phosphorus: An Effective Feedstock for the Synthesis of Phosphorus-Based Chemicals

CCS Chemistry ◽  
2019 ◽  
Vol 1 (2) ◽  
pp. 166-172 ◽  
Author(s):  
Lie Wu ◽  
Shi Bian ◽  
Hao Huang ◽  
Jiahong Wang ◽  
Danni Liu ◽  
...  
Keyword(s):  
Organophosphorus Compounds ◽  
Black Phosphorus ◽  
White Phosphorus ◽  
The Novel ◽  
Phosphine Oxides ◽  
Elemental Phosphorus ◽  
One Pot ◽  
Mild Conditions ◽  
Novel Concept ◽  
Phosphine Sulfide

We propose and demonstrate the novel concept of synthesizing organophosphorus compounds directly from black phosphorus (BP) nanoparticles as the feedstock. Compounds such as alkyl phosphines, alkyl phosphine oxides, phosphine sulfide, and hexafluorophosphate anion are prepared with good isolation yields under mild conditions. Selective synthesis of primary, secondary, and tertiary organophosphorus compounds is also demonstrated utilizing this one-pot approach. Reaction mechanisms are proposed and discussed. Compared with traditional white phosphorus (P4)-based methods, the new synthetic concept and process utilizing elemental phosphorus are more efficient and environmentally friendly.

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 &#945;-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 &#945;-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.

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