Application Of Diarylation Reaction Of Glycine Derivative α-C(sp3)-H In The Synthesis Of Diarylmethane Derivatives

As an important structural framework,diarylmethane not only widely exists in a variety of alkaloid natural products,but also exists in clinically commonly used small molecule drugs and their derivatives.As a result,many research groups have been attracted to carry out synthetic research on its skeleton construction.The cross-dehydrocoupling reaction(CDC)of glycine derivatives and electron-rich aromatic hydrocarbons has became a very promising method for the synthesis of diarylmethane derivatives,because it can effectively avoid problems such as the danger of reaction raw materials and the need for pre-functionalization of reaction substrates.At present,there are few reports on the synthesis of gem-diarylmethane derivatives by this method,and the method of synthesizing asymmetric gem-diarylmethane derivatives by this method has not been reported yet.In order to further expand the application of glycine derivatives in the synthesis of diarylmethane derivatives,the following two synthetic methods have been developed in this paper:The first synthetic method is to synthesize diverse geminal diarylmethane derivatives by double Friedel-Crafts alkylation between a glycine derivative and N-substituted aniline under the synergistical catalysis of HFIP-K2S2O8.This reaction does not need to add transition metal catalysts,has high selectivity and wide applicability.And the yield of products is good to excellent.The second synthesis method is to synthesize a series of geminal diarylmethane derivatives and asymmetric geminal diarylmethane derivatives by the CDC between glycine derivatives and electron-rich aromatic hydrocarbons(including N-substituted anilines,primary aromatic amines,indole,etc.)under the catalysis of AlCl3.This reaction also does not require additional transition metal catalysts,obtains highly selective products with moderate to excellent yields and wider substrate applicability.And this reaction is environmentally friendly.