Nucleophilic H-phosphites, H-phosphinates and H-phosphine oxides in organic reactions

Synthesis ◽  
2021 ◽  
Author(s):  
Zhan-Yong Wang ◽  
Qi Guo ◽  
Shaohong Xu ◽  
Kai-Kai Wang
Keyword(s):  
Aryl Halides ◽  
Organic Reactions ◽  
Diazo Compounds ◽  
Phosphine Oxides ◽  
Sulfonyl Chlorides ◽  
Iodonium Salts ◽  
Unsaturated Compounds

P(O)-H compounds like H-phosphites, H-phosphinates and H-phosphine oxides are widely used as nucleophiles. Herein, reactions with unsaturated compounds, C-H activation, Hiro reaction, P-C, P-S, P-O, P-N and P-F couplings were thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propiolic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols and thioalcohols.

Microwave irradiation and catalysis in organophosphorus reactions

2019 ◽  
Vol 91 (1) ◽  
pp. 145-157 ◽  
Author(s):  
György Keglevich ◽  
Nóra Zsuzsa Kiss ◽  
Réka Henyecz ◽  
Zoltán Mucsi
Keyword(s):  
Microwave Irradiation ◽  
Aryl Halides ◽  
Arbuzov Reaction ◽  
Phosphine Oxides ◽  
Direct Esterification ◽  
Phosphinic Acids ◽  
Mw Irradiation ◽  
Organophosphorus Chemistry ◽  
Active Methylene ◽  
The Arbuzov Reaction

AbstractThe usual advantage of microwave (MW) assistance is making organic reactions faster and more efficient. In this article we present reaction types from organophosphorus chemistry, when MW-assisted transformations (e.g. the direct esterification and alkylating esterification of phosphinic acids) may be promoted by suitable catalysts, or vice versa, when a catalytic reaction is enhanced by MW irradiation (e.g. the Arbuzov reaction of aryl halides), and when catalysts may be omitted or simplified under MW irradiation as shown by the alkylation of active methylene containing P=O substrates/the Kabachnik–Fields reaction/deoxygenation of phosphine oxides, and the Hirao reaction, respectively.

Visible light-promoted reactions with diazo compounds: a mild and practical strategy towards free carbene intermediates

2020 ◽  
Vol 49 (19) ◽  
pp. 6833-6847 ◽  
Author(s):  
Zhen Yang ◽  
Mateus L. Stivanin ◽  
Igor D. Jurberg ◽  
Rene M. Koenigs
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Reactive Intermediates ◽  
Organic Reactions ◽  
Light Irradiation ◽  
Diazo Compounds ◽  
Practical Strategy ◽  
Key Features

Carbenes generated from visible light irradiation are readily accessible, highly reactive intermediates that have been recently applied in several organic reactions. An overview of the field including key features and examples is provided herein.

P-Arylation of secondary phosphine oxides catalyzed by nickel-supported nanoparticles

2018 ◽  
Vol 5 (13) ◽  
pp. 2079-2085 ◽  
Author(s):  
Elżbieta Łastawiecka ◽  
Anna Flis ◽  
Marek Stankevič ◽  
Magdalena Greluk ◽  
Grzegorz Słowik ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Supported Nanoparticles ◽  
Ligand Free

Nickel-supported nanoparticles were used as catalysts for ligand-free Hirao coupling between secondary phosphine oxides and aryl halides.

scholarly journals Recent Advances in the Synthesis of Sulfides, Sulfoxides and Sulfones via C-S Bond Construction from Non-Halide Substrates

Catalysts ◽  
2020 ◽  
Vol 10 (11) ◽  
pp. 1339
Author(s):  
Rui Zhang ◽  
Huaiwei Ding ◽  
Xiangling Pu ◽  
Zhiping Qian ◽  
Yan Xiao
Keyword(s):  
Coupling Reaction ◽  
Aryl Halides ◽  
Diazo Compounds ◽  
Reaction Pathways ◽  
Easy Access ◽  
Thiyl Radicals ◽  
Recent Advances ◽  
Sulfur Containing ◽  
Powerful Strategy ◽  
Sulfur Containing Compounds

The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, providing easy access to sulfur containing compounds. Unlike traditional Ullmann typed C-S coupling reaction, the recently developed reactions frequently use non-halide compounds, such as diazo compounds and simple arenes/alkanes instead of aryl halides as substrates. On the other hand, novel C-S coupling reaction pathways involving thiyl radicals have emerged as an important strategy to construct C-S bonds. In this review, we focus on the recent advances on the synthesis of sulfides, sulfoxides, and sulfones from non-halide substrates involving C-S bond construction.

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