Ph3P-mediated highly selective C(α)–P coupling of quinone monoacetals with R2P(O)H: convenient and practical synthesis of ortho-phosphinyl phenols

2018 ◽  
Vol 20 (22) ◽  
pp. 5111-5116 ◽  
Author(s):  
Ruwei Shen ◽  
Ming Zhang ◽  
Jing Xiao ◽  
Chao Dong ◽  
Li-Biao Han
Keyword(s):  
Coupling Reaction ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Practical Synthesis

The Ph3P-mediated C(α)–P coupling reaction of quinone monoacetals with secondary phosphine oxides is developed to provide an effective method for the synthesis of a wide array of ortho-phosphinyl phenols in good to excellent yields.

Zinc-catalyzed regioselective C–P coupling of p-quinol ethers with secondary phosphine oxides to afford 2-phosphinylphenols

2019 ◽  
Vol 17 (11) ◽  
pp. 2972-2984 ◽  
Author(s):  
Ming Zhang ◽  
Xiaoyu Jia ◽  
Haowei Zhu ◽  
Xutong Fang ◽  
Chenyi Ji ◽  
...  
Keyword(s):  
Synthesis Method ◽  
Coupling Reaction ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
New Synthesis

A highly regioselective C–P coupling reaction of p-quinol ethers with secondary phosphine oxides is developed as a new synthesis method for 2-phosphinylphenols by using Zn(OTf)2 as the catalyst.

Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

2017 ◽  
Vol 68 (1) ◽  
pp. 180-185
Author(s):  
Adriana Maria Andreica ◽  
Lucia Gansca ◽  
Irina Ciotlaus ◽  
Ioan Oprean
Keyword(s):  
Sex Pheromone ◽  
Coupling Reaction ◽  
Coupling Scheme ◽  
Lithium Aluminium Hydride ◽  
Terminal Alkyne ◽  
Mercury Derivative ◽  
Lithium Aluminium ◽  
Convenient Synthesis ◽  
Practical Synthesis ◽  
Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

scholarly journals Microwaves as “Co-Catalysts” or as Substitute for Catalysts in Organophosphorus Chemistry

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1196
Author(s):  
György Keglevich
Keyword(s):  
Coupling Reaction ◽  
Diels Alder ◽  
Typical Case ◽  
Conventional Heating ◽  
Phosphine Oxides ◽  
Phosphonic Acids ◽  
Co Catalysts ◽  
Mw Irradiation ◽  
Organophosphorus Chemistry ◽  
Hydrolysis Of

The purpose of this review is to summarize the importance of microwave (MW) irradiation as a kind of catalyst in organophosphorus chemistry. Slow or reluctant reactions, such as the Diels-Alder cycloaddition or an inverse-Wittig type reaction, may be performed efficiently under MW irradiation. The direct esterification of phosphinic and phosphonic acids, which is practically impossible on conventional heating, may be realized under MW conditions. Ionic liquid additives may promote further esterifications. The opposite reaction, the hydrolysis of P-esters, has also relevance among the MW-assisted transformations. A typical case is when the catalysts are substituted by MWs, which is exemplified by the reduction of phosphine oxides, and by the Kabachnik–Fields condensation affording α-aminophosphonic derivatives. Finally, the Hirao P–C coupling reaction may serve as an example, when the catalyst may be simplified under MW conditions. All of the examples discussed fulfill the expectations of green chemistry.

Thermal stability of primary and secondary phosphine oxides formed as a reaction of phosphine oxide with ketones

2016 ◽  
Vol 191 (11-12) ◽  
pp. 1480-1481 ◽  
Author(s):  
E. V. Gorbachuk ◽  
E. K. Badeeva ◽  
S. A. Katsyuba ◽  
P. O. Pavlov ◽  
Kh. R. Khayarov ◽  
...  
Keyword(s):  
Thermal Stability ◽  
Phosphine Oxide ◽  
Secondary Phosphine ◽  
Phosphine Oxides ◽  
Thermal Stability Of
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