Cross-coupling Of Electrophilc Compounds And N-haloimides Enabled By Halogen Bonding

Phthalimides compounds as a kind of important organic synthetic raw material and intermediate,has important application in the field of medicine,pesticide,organic materials and other fields.As a result,the methods of synthetic for this type of compounds has received widespread attention for chemists.This paper presents a model of halogen bonding activation,achieves the cross-coupling of electrophilic compounds alkyl halide and N-haloimides,provides a new method to synthesis phthalimides compounds.The synthesis method has the advantages of fast and high efficiency,metal free,mild reaction condition,broad scope of substrate in terms of both alkyl halide and N-haloinide and high utilization rate of the atom.When DBU was added,the cross-coupling reaction between electrophilic compounds and N-haloimides occurred,resulting in the formation of aminated products.The best condition of reaction with dimethyl sulfoxide as solvent,1.2 equiv N-haloimides,1.2 equiv DBU and 1.0 equiv alkyl halides at room temperature,with good yield of target product(25%-93%).The experimental results show that alkly halide RX(X=Cl,Br,I)exhibit increased reactivity in the order of RCl,RBr and RI.The reaction activity of N-haloimides: N-choloimides works better than N-bromoimides.On this basis,this paper puts forward the mechanism of mutual activation induced by halogen bonding to promote cross-coupling reaction.The presence of halogen bonding activates N-haloimides and substrate alkyl halides,makes the reaction can be efficient smoothly.The synthesis method and the mechanism of this method have been proposed to enrich the halogen bond chemistry,represents an elegant example of applying the halogen bonding activation strategy in organic transformation.