Study On The Solvent-free For "One-pot" Synthesis Of Homoallylic Alcohol And High Propargyl Alcohol Mediated By Tin Powder

In organic chemistry, the formation of carbon-carbon bond is an important way tobuild a molecular skeleton, allylation and propargylation of the carbonyl compoundsare the important methods for the formation of carbon-carbon bond. Due to thehomoallylic or homopropargyl alcohols containing a hydroxyl group andcarbon-carbon double bond or carbon-carbon triple bond, they often applied inconstruction biologically active compounds such as macrocyclic lactone, polyhydroxysteroid natural products and polyether antibiotics. Being important buildingblocks and versatile synthons, homoallylic and homopropargylic alcohols are highlyfeatured in the organic syntheses. Among the existing means of constructionhomoallylic and homopropargylic alcohols, metal-mediated allylation andpropargylation of the carbonyl compounds is one of the most convenient and easiestmethods.In organic synthesis, the organic solvent used in reaction can disperse reactants tomedium in the same phase, but it is toxic and difficult to recover and harmful to theenvironment. Some green mediums may be used such as water, liquid carbon dioxideand ionic liquid, but some reagents are sensitive to water and air. Solventless reactionmay be the alternative strategies. Moreover, with the absence of solvent molecules,high concentration of the reactants can be obtained, the reaction rate can beeffectively improved; ordered molecules may be useful to increase the selectivity ofthe reaction and also be useful to reduce the occurrence of side reactions, whichwould simplify the operation.This paper investigated the environment-friendly Barbier-type reactions of thecarbonyl compounds promoted by tin powder under solvent-free conditions. Thepresent method uses inexpensive tin powder, avoiding the use of volatile toxic organictin reagent, and provides a green synthesis of homoallylic and homopropargylicalcohols. This thesis includes three chapters:Chapter One: Recent Developments of the Allylation Reactions of CarbonylCompounds Mediated by Organometalics.This chapter reviews the progress of allylation reactions of carbonyl compounds inrecent years. A detailed overview of allylation reactions of carbonyl compoundspromoted by different metals has been viewed.Chapter Two: Study on Reaction of Carbonyl Compounds and Allyl bromideMediated by Tin Powder under Solvent-free conditions.This chapter investigated the homoallylation of aldehydes and ketones with allylbromide promoted by tin powder under solvent-free conditions. The method has theadvantage of short reaction time, high yields, easy operation. Not only aromaticaldehydes, but also heterocyclic aldehydes, aliphatic aldehydes, and ?,?-unsaturatedaldehyde can be allylated with allyl bromide.Chapter Three: Study on Reaction of Carbonyl Compounds and PropargylBromide Mediated by Tin Powder under Solvent-free conditions.This chapter studied the reaction of aldehydes and ketones with propargylbromide at room temperature in the presence of tin powder under solvent-freeconditions. The method is simple, less time-consuming. Not only aromatic aldehydes,but also heterocyclic aldehydes, aliphatic aldehydes, and ?,?-unsaturated aldehydecan be propargylated with propargyl bromide.