Studies On The Synthesis Of Aliphatic Esters By Photocatalyzed Alkoxycarbonylation Of Alkenes

Aliphatic esters not only widely exist in various aspects of production and life such as pesticides,medicines,materials,food chemistry,flavors and fragrances,but also are extremely important chemical raw materials.Therefore,the efficient synthesis of ester compounds has great research value.The traditional esterification reaction conditions are mild,but the carbonyl structure needs to be introduced in advance.The Reppe carbonylation reaction substrate is simple and easy to obtain,but it requires the use of flammable and explosive carbon monoxide gas,the reaction conditions are harsh,and there is a problem of regioselectivity.Compared with these synthetic methods,photocatalytic radical reactions have many advantages,such as mild reaction conditions,good atom economy,and good regioselectivity.The main research content of this dissertation is to realize the alkoxycarbonylation of alkenes and construct a series of carboxylate compounds by using simple and readily available alkyloxalyl chlorides as the precursors of alkoxycarbonyl radical This paper is mainly divided into the following three parts:In the first part,visible light catalyzed alkoxyacyl chlorination of alkenes to synthesizeβ-chlorocarboxylic acid esters.In this chapter,alkyloxalyl chlorides were used as the source of alkoxycarbonyl radical to realize the alkoxycarbonylation of alkenes to construct a series of β-chlorocarboxylic acid esters and α,β-unsaturated carboxylic acid esters.We applied this method to synthesize bioactive molecule dihydronaphthalene derivatives and antithrombotic drug ozagrel.At the same time,a series of studies on the reaction mechanism were also carried out.The second part,visible light-catalyzed alkoxycarbonylation to synthesize oxindoles.In this chapter,the visible-light-catalyzed alkoxycarbonylation/cyclization of N-arylacrylamides was developed,and a series of ester-substituted oxindoles and furinoindolines were prepared.At the same time,the natural product(±)-Physovenine was synthesized in the form.The third part,visible light catalyzed alkoxycarbonylation to synthesize ester-substituted indolo [2,1-a]isoquinolines.In this chapter,In this chapter,the visible-light-catalyzed alkoxycarbonylation/cyclization of 2-arylindole compounds is developed.This reaction can easily and efficiently construct a variety of ester-substituted indole[2,1-a]isoquinolines from indole compounds under mild conditions.The method has broad functional group compatibility and high efficiency.