Development Of Novel Arylation Reactions With Diaryliodonium Salts

Diaryliodonium salts,as one of the best known componds in iodine(III)class,are widely used as versatile arylating agents in organic synthesis.In terms of synthetic disconnections involving aryl groups,the formation of an aryl electrophile is more challenging than the formation of an aryl nucleophile.Diaryliodonium salts can offer an alternative approach to deliver reactive aryl electrophile which enables these iodine(III)reagents to realize aryl group transformations under mild conditions.Due to the facile preparation to approach diaryliodonium salts,combined with their property of being air and moisture-stable,it is worth making deeper investigation on these arylation reagents.In order to further promote the application of these reagents,we have conducted the research work developing novel arylation reacting pattens involving diaryliodonium salts.The main contents of research work in this dissertation are as follows:1)Instead of mono aryl-coupling between the substrates and aryl electrophiles,a diret vicinal disubstitution of diaryliodonium salts has been realized via the reactions with pyridine N-oxides and N-amidates.Such synthetic method proved to be an efficient approach to ortho-disubsituted benzene derivaties under the metal-free condition.The alternative disubstitution of the aryl species has leveled up the variety of the aryl transfering form of diaryliodonium salts.2)For the aim of developing step-ecnocmic reactions,we have seeked for the better application of diaryliodonium salts to tandem reactions.A copper-catalyzed arylcarbocyclization method of alkynes substrates with diaryliodnium salts has been described here in the thesis.Two C-C bonds have been formed in one step in addition that the inert C-H bonds on the alkyl chains have been activated to selective form five-membered rings.3)The use of the high reactivity on diaryliodonium salts has been better made by succefully applying them to activate inert C(sp~3)–H bonds of oxime ethers in an?-arylation process.In accordance with more efficient and step-ecnomic synthetic trategies,diaryliodonium salts have showed as the privileged reagent in C(sp~3)–H bond activation reactions via removable directing group.The easy manipulation enabled the method to modify a number of natural backboned compounds while the advantage of diaryliodonium salts has been largly extended.