Study On The Reaction Of Silver-catalyzed Regioselective Hydroboration Of Unsaturated Hydrocarbon

Organoboron compounds and their derivatives have always played an important role in organic synthetic chemistry because they can be used to construct various organic compounds such as carbon-carbon and carbon-heteroatoms(oxygen,sulfur,nitrogen,etc.).Chemical bonds,which enable multiple types of chemical transformations,are essential synthetic intermediates in the fields of organic chemistry,medicinal chemistry and materials.Among them,alkenyl groups and alkyl boron ester compounds have been widely concerned in synthesis and application because of their advantages such as easy handling,insensitivity to air and water,and easy separation and preservation.Alkenyl and alkyl boron ester compounds are conventionally synthesized by reacting a suitable boric acid derivative with a highly reactive main group organometallic reagent such as a format reagent and an organolithium reagent,but due to lack of functional group tolerance,Limits its scope of application in synthesis.Catalytic hydroboration with unsaturated hydrocarbons as a starting material provides a simple,efficient and atom-economic process for the preparation of alkyl and alkenyl boron esters by continuous carbon-carbon and carbonThe construction of heteroatom bonds enables the conversion of a variety of functional groups.Therefore,the search for a new catalytic system to selectively catalyze the hydroboration of unsaturated hydrocarbons has become a long-term research topic in academia and industry.In the past few decades,many catalytic systems,including precious metals,abundant metals on earth,and rare earth metal catalysts,have been studied in detail on the hydroboration of unsaturated hydrocarbons.At present,metallic copper has achieved good results in catalyzing the hydroboration reaction,and silver as a metal of the same subgroup,its catalytic hydroboration reaction has rarely been reported in the synthesis of organoboron compounds.On this basis,we The silver catalytic system was thoroughly and systematically studied.Here,we report the use of a silver salt as a catalyst for the regioselective hydroboration addition of a boronic ester with an unsaturated hydrocarbon.This method does not require the participation of ligands and bases,and provides an efficient and practical method for the synthesis of alkyl,homoallyl and alkenyl borate compounds having regioselectivity and stereoselectivity.