Study On A Novel Coupling Reaction System Of Arylboronic Acids With Tosylhydrazones

Carbene is a kind of crucial organic synthetic intermediate,which prove to be extensive applications in organic synthesis,medicinal chemistry,materials chemistry for its various reactivity and a succession of related organic reactions were developed in the last decades.Especially,the transition-meta-free cross-coupling reactions of tosylhydrazones as carbene precursors had been extensively developed in recent years.This kind of reactions have a wide application prospect in organic synthesis.Based on the previous studies,the cross-coupling reactions between arylboric acids with tosylhydrazones were expanded in this paper.The specific contents are as follows:Firstly,a series of(25)?-arylalkylferrocenes were synthesized by the cross-coupling between acylferrocene sulfonylhydrazones and arylboronic acids with a wide range of substrate adaptability and functional group tolerance including several anticancer molecules.Finally,a plausible mechanism of the CsF-promote reaction process was proposed.Secondly,a synthetic strategy of 3-arylindanones via reductive cross-coupling of monocondensation 1,3-indanediones with boronic acids had been established and a series of 3-arylindanones had also been afforded with moderate to excellent yields.The synthetic strategy has advantages such as good functional group tolerance and wide substrate scope,simple experimental conditions,portable substrates and provides a new method for construction of 3-arylindanones.Lastly,a tandem transition-meta-free strategy of reductive cross-coupling of arylboric acid with tosylhydrazone and additive reaction between alkylboric acid with cyano group in the same molecule was established.The strategy has advantages such as good functional-group tolerance and wide substrate scope;we proposed and designed experiments to verify the possible reaction mechanism of this reaction,and provided reference for the study of this kind of reactions in the future.In conclusion,a series of alkylferrocenes and 3-arylindanones were synthesized by crosscoupling reaction of tosylhydrazones with arylboric acids,and the application scope of this kind of reaction was extended in this paper.A tandem reaction between tosylhydrazones with arylboric acids and additive reaction between alkylboric acids with cyano group in the same molecules were studied,which provided a reference for further study on this kind of reactions.