Synthesis Of β-borone By Boron Carbonylation Of Alkynes With Aromatic Diazonium Salts

At present,the source of commodity chemicals mainly relies on non-renewable resources such as coal and oil,so it is necessary to find ways to slow down their use in today’s increasingly serious energy crisis.C1 small molecules such as carbon monoxide,carbon dioxide,methane and methanol can be used as options for sustainable development.Among them,carbon monoxide has become the preferred object of chemical workers because of its easy activation and relatively easy to obtain,and has made great achievements in industry and academic,such as: Fischer-Tropsch synthesis,hydroformylation,Reppe reaction and Monsanto reaction and its improvement method.In addition,the construction of boron-containing organic molecules has been a hot and important research field.This is because it is not only widely used in drugs,materials and organic synthesis,but also as an important intermediate in organic chemistry,such as: Suzuki-Miyura coupling construction of C-C bond,C-X construction and Cheteroatomic bond construction.In addition,organoborate compounds are non-toxic to human,animal,plant and other complex organisms,which also accords with the concept of green chemistry.After several decades of development,the borylation of alkynes has become relatively mature.However,chemists are not satisfied with this,and put forward higher requirements,and began to pursue the difunctional synthesis of alkynes into organoborate compounds.Because this synthesis method can efficiently add two functional groups to the C-C triple bond through a one-step reaction,so as to quickly construct complex and multi-functional organic molecules,so it has attracted more and more attention of chemical researchers.At present,with the unremitting efforts of organic chemists,great progressions have be made in this field.In many synthesis reactions,the products are alkenyl boron compounds,but the one-step synthesis of bifunctional alkyl boron compounds has not been reported.In this paper,we developed a method for synthesizing saturated β-borone compounds using acetylene,carbon monoxide,bifinatol diester and aryl diazo salt as substrates and palladium/copper cocatalyzed.In addition,the system is suitable for a wide range of substrates and has good functional group tolerance.At the same time,we also studied the mechanism and showed that the hydrogen of the product came from ethyl acetate.