Copper Catalyzed Alkynylboration And Thioboration Of Unsaturated Carbon-carbon Bonds

With the development of the organic chemistry,organic boronate esters have become attractive organometallic nucleophiles due to its mild Lewis acidity,nice stability,and controllable reactivity.Meanwhile,as the derivatives of boronic acids,boronate esters are also a sort of low-toxic and environment-friendly green organic molecule which play an important role in the synthesis of drugs and materials.The addition of boron reagents to unsaturated carbon-carbon bonds is a powerful method for the preparation of organic boronates.In recent years,the development of borylation and functionalization of unsaturated carbon-carbon bonds has not only expanded the synthesis method of organic boronate esters,but also provided more possibilities for the transformation.In the first chapter,We reviewed the literature concerning the current advances in the borylation and functionalization of unsaturated carbon-carbon bonds.With distinguishing different functional groups involved in the functionalization,we can understand the background much better,and it would be more easy for us to find the key point in this field.Vinylboronates are widely used in the total synthesis of natural products.Acetylene,as a bulk chemical product,is also an important raw material for organic synthesis,the efficient use of acetylene has a high economic value.In the second chapter,we realized the copper-catalyzed Alkynylboration reaction of acetylene.The reaction uses alkynyl bromide,acetylene and bis(pinacolato)diboron as the raw materials to obtain cis alkynyl-alkenyl-boronates with single selectivity.Thioboration of unsaturated carbon-carbon bonds is an effective means of preparing thioether derivatives.In the third chapter,we achieved the copper-catalyzed Thioboration reaction of styrene derivative.The reaction uses substituted styrene,S-(alkyl)benzenesulfonothioate electrophiles and bis(pinacolato)diboron as the raw materials to obtain thioboration products of styrene with high regioselectivity.