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Green Synthesis Of Carboxylic Acid Esters And Phosphate Ester Compounds Which Have Diversified Structures

Posted on:2021-01-22Degree:MasterType:Thesis
Country:ChinaCandidate:F HouFull Text:PDF
GTID:2381330623482106Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Esters are an important organic synthesis intermediates.It is widely used in the fields of medicine,natural products,dyes and optoelectronic synthesis.In particular,organic phosphate compounds and their derivatives have important application value in many fields such as pesticides and fireproof materials.For a long time,various ester synthesis methods have attracted great attention from researchers and finding efficient and simple synthesis methods has attracted more and more attention from chemical researchers.The main content and results of this thesis are as follows:1.The research progress of synthesis of carboxylic acid esters,phosphates/hypophosphites,and phosphorothioates in recent years is summarized.2.An environmentally friendly oxone catalyzedesterification of carboxylic acids with alcohols has been researched.A series of carboxylic acid esters are obtained in high yield.This strategy requires mild reaction conditions,providing an attractive alternative for the construction of valuable carbonyl esters.Electron-rich and electron-deficient groups are compatible with the standard conditions and a variety of substrates are demonstrated.Moreover,the reaction could easily be adapted to typical prodrugs,drugs and gram-scale synthesis.3.Using diphenyl disulfide compound as an accelerator,the alkylation product of N-arylphosphoroformamide reacts with an alcohol.At room temperature,the carbonyl C-P bond is broken and the P-O bond is constructed in one pot.A series of alkyl phosphates and hypophosphites were prepared with moderate to excellent yields,and theoretical calculations proved the possibility of carbonyl C-P bond breakage in N-arylphosphoroformamide.At the same time,a simple and efficient method for building C-P(III)bonds was developed by using the Michael addition reaction of N-arylphosphamide withα,β-unsaturated carbonyl compounds,and a variety of P-functionalized phosphorus was synthesized Amide compounds.4.Using the inorganic substance NaOCP(dioxane)2.5 as the"P"source,reacted with diphenyl disulfide under metal-free conditions,a variety of phosphorothioate products were obtained in moderate to good yields.The structure of some products was confirmed by X-ray.The conversion from inorganic phosphorus to organic phosphorus is realized,which opens up a new direction for the application of NaOCP(dioxane)2.5.The structure of the above target product was confirmed by 1H NMR,13C NMR,31P NMR and HRMS.
Keywords/Search Tags:Oxone, carboxylic acid ester, phosphate/phosphite, diphenyl disulfide, metal-free
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