Tin Powder Promoted Synthesis Of α-Trifluoromethyl Homoallylic Alcohols,Homopropargylic Alcohols And Homoallylic Hydrazides

Organofluorine compounds have been found increasing applications in industrial fields such as the pharmaceutical and medicinal chemistry and material sciences. There are two main ways of introducing trifluoromethyl group into complex organic molecules. One is the direct introduction of trifluoromethyl group, by using either nucleophilic or electrophilic trifluoromethylation reagents, or radical trifluoro-methylation reagents, into complex organic backbone. The other is the use of trifluoromethylated building blocks to construct organofluorine compounds. We explored synthesis of α-trifluoromethyl homoallylic alcohols, α-trifluoromethyl homopropargylic alcohols and α-trifluoromethyl homoallylic hydrazides promoted by tin power. The thesis includes four chapters: Chapter one: The studies of trifluoromethylation reaction using trifluoromethyl ketones and their derivatives as building blocksIn this chapter, we discussed the development of trifluoromethylation reaction using trifluoromethyl ketones and their derivatives as building blocks. Chapter two: The synthesis of α-trifluoromethyl homoallylic alcohols and α-trifluoromethyl homopropargylic alcohols promoted by tin powerThis chapter explores the synthesis of α-trifluoromethyl homoallylic alcohols and α-trifluoromethyl homopropargylic alcohols promoted by tin power. This method has advantages of short reaction time, high yields, and easy operation. Chapter three: Tin-mediated four-component “one-pot” synthesis of homoallylhydrazides from aryl trifluoromethyl ketones, aryl acylhydrazines and allyl bromide.This chapter explores the four-component “one pot” synthesis of α-trifluoromethyl homoallylic hydrazides from tin power, trifluoromethyl ketones, hydrazines, and allyl bromide. α-Trifluoromethyl homoallylic hydrazides are important natural products. This tin promoted process has the following features: metal catalyst-free, operational simplicity, high yields and avoidance of preparation of allyltin reagents beforehand. Chapter four: The synthesis of α-trifluoromethyl ketones initiationed by TBPA+.This section explores the synthesis of α-trifluoromethyl ketones from styrene as raw material and sodium trifluoromethanesulfinate initiationed by TBPA+.. It offered a novel method for the synthesis of α-trifluoromethyl ketones.