Synthesis Of Carbonyl And Quinoline Compounds Based On Ruppert-Prakash Reagent And Alkyne/Carboxylic Acid

The introduction of fluorine with high electronegativity and low polarizability into organic compounds can give them unique properties,such as lipophilicity,metabolic stability,and antioxidant properties,as well as high physical and chemical stability.These characteristics make it often used in fields such as medicine,pesticide,and material science.Therefore,the research on fluorine-containing reagents and fluorine-containing compounds has always been favored by researchers in various fields.As for the Ruppert Prakash reagent,which is cheap and easy to store,many chemists use it to prepare different kinds of products with more synthetic value and application value.And,carbonyl and quinoline derivatives are widely found in natural products and drug molecules,not only have good biopharmacological activity but also play an important role in organic molecule synthesis as efficient catalysts or ligands in organic synthesis building blocks.Based on this,the use of the Ruppert Prakash reagent to efficiently synthesize derivatives with carbonyl and quinoline skeletons has always been the goal pursued by organic chemists.In this paper,based on the Ruppert Prakash reagent,a convenient,safe and operable scheme is proposed to build a complex and novel α,β-Unsaturated aldehydes,enol esters,iodoalkyl esters,and quinoline derivatives.The main research results of this paper are as follows:(1)A new scheme for the synthesis of versatile electrophiles(E)-β-iodo-α,β-unsaturated aldehyde from terminal alkynes,Ruppert Prakash reagent,and sodium iodide under the catalysis of copper was proposed.This scheme not only shows good substrate universality and functional group tolerance,but also has excellent chemical selectivity,regional selectivity and stereoselectivity.And,as an(E)-β-iodo-α,β-unsaturated aldehyde with multiple reaction sites,its application value has been proved by application transformation and drug molecule synthesis.(2)A new method for the synthesis of(Z)-trifluoromethyl enol ester by copper-catalyzed Ruppert Prakash reagent and cheap carboxylic acid was developed for the first time.This method not only has the advantages of easy availability of raw materials,mild conditions,and simple operation but also has high chemical selectivity,regional selectivity,and stereoselectivity.This(Z)-trifluoromethyl enol ester synthesis strategy opens the door to the construction of highly functionalized or complex enol esters that are still difficult to prepare by conventional synthesis methods.(3)A new scheme for constructing iodoalkyl ester compounds from biomass derivatives cyclic ethers and carboxylic acids was realized.In this mechanism,the Ruppert Prakash reagent plays a key role as the acceptor of the cyclic ether oxygen atom.This scheme not only improves the step economy and synthesis efficiency of these compounds but also has broad substrate universality,functional group tolerance,and transformation practicality.And,solve the challenge of selectively removing oxygen from cyclic ethers to obtain high-value-added chemicals.(4)A new strategy for the synthesis of 2-alkoxy-3-substituted quinolines by cyclization of 2-alkynylaniline derivatives with Ruppert Prakash reagent was developed.This reaction has the advantages of wide substrate universality,high tolerance of functional groups,simple conditions,and easy operation.