Synthesis Of Alkynyl Sulfones And Alkynyl Phosphonates And Researches On The Methodology

Alkyne compounds are not only found in natural products,but also in the fields of biomedicine,pesticides,photovoltaic materials and organic synthesis intermediates.The acetylene compound is like a broad-leaved tree,and the alkyne substituted by a hetero atom is a very important and lush branch.This kind of compounds has both the full properties of the alkyne and the characteristics of the hetero atom.Such compounds can be subjected to an addition reaction,a cycloisomerization reaction,a cycloaddition reaction,a polymerization reaction,and a redox reaction.Among them,alkynyl sulfones and alkynyl phosphonates are two very important acetylene compounds.The sulfur atom and phosphorus atom ar e directly connected to the unsaturated carbon-carbon triple bond.The structure is special,which is a synthetic sulfur-containing organic compound and a phosphorus-containing organic important intermediates.In addition,sulfur and phosphorus are widely present in trace elements in various organisms.Alkynyl sulfones and alkynyl phosphonates compounds have excellent biological activity and have great research value and application prospects in the life science field.Nowadays,the concepts of green chemistry and atomic economics are deeply rooted in people's minds.Synthetic methods with economical advantages,simple operation,mild conditions,less side reactions,and high yield have become the trend of many researches.The"one-pot method"successfully produced arylethynyl sulfides,yamines and symmetrical dialkynyl selenides.Therefore,based on the work of the laboratory over the years and a large number of literature research,this paper proposes a new method for the synthesis of c and alkynyl phosphon ates compounds by using Mukaiyama reagent.In this paper,the following researches have been carried out on the green synthesis methodology and reaction mechanism of alkynyl sulfones and alkynyl phosphonates:Firstly,this paper introduces the background of the research and the significance of the research.Compared with the traditional synthetic methods,using the Mukaiyama regent the green synthesis method has lots of advantages.Finally we established the research direction and content of this paper.In this paper,the aryl ketone is obtained from the cheap and easily available aryl ethyl ketone,which is brominated to obtain hydrazine-bromo aryl ketone,which is then reacted with sodium sulfinates to obtain a series of aryl acetyl sulfones,which are then highly active.Using aryl acetyl sulfone as a raw material,finally we established the optimal conditions for green synthetic acetylene sulfone compounds through a series of comparative tests.Under the optimal conditions,Mukaiyama reagent,triethylamine and substrate aryl acetyl sulfone were added into the same reactor,and a series of alkynyl sulfones compounds were finally synthesized by eliminating reaction.Similarly,aryl ketone is used as a raw material to obtain ruthenium-bromo aryl ketone by bromination reaction,and then reacted with phosphite to obtain a series of aryl acetyl phosphonates.Under the optimal conditions previously explored,Mukaiyama reagent,triethylamine,and substrate arylacetylphosphonate were added to the same reactor,and a series of alkynyl phosphonates compounds were finally synthesized.Compared with the conventional method for synthesizing an alkynyl phosphonate compound,the method has the advantages of mild conditions,simple operation,environmental friendliness,and low cost of raw materials.This method not only provides a simple and efficient new way to synthesize alkynyl sulfones compounds,but also provides a new method for synthesizing alkynyl phosphonates compounds.Based on the original laboratory,this paper investigates a large number of literatures and proposes the possible reaction mechanism of the method.All the target compounds synthesized in this thesis were characterized by IR,¹H NMR,¹³C NMR,³¹P NMR,MS and HRMS.