Studies On Cu I Catalysed Regio And Stereo Selective Hydroboration Of Ynamides

Abstract

During the last few decades, organoboron compounds have attracted an extraordinary level of attention due to their importance to organic synthesis, medicinal chemistry, materials and the range is staggering. In particular, vinylogous boron compounds are essential and versatile building blocks for a wide range of organic synthetic requirements and play a vital role in the construction of complex molecular architecture. Traditionally several methods such as reacting alkenyl active metal compounds with B(OH)3, Pd/Pt catalysed halogen exchange with HB(OR)2, olefinic cross metathesis are used for synthesis of vinylboronate compounds. However, limited structural diversities of the substrate or the requirement of prefunctionalised stating materials are the major constraints of these methods. Therefore, new alternate efficient methods to synthesize vinylogous boron compounds become necessity of the moment. One such method is hydroboration of alkynes, which proceeds under tunable and mild reaction condition. Hydroboration of internal alkynes, combined with required organic transformations of the carbon - boron bond of the product becomes as important method for synthesizing trisubstituted alkenes with defined configurations. newlineIn recent years several elegant efforts have been delineated by several research groups toward the hydroboration of alkynes, as this is the most straight forward and efficient approach towards construction of vinyl boronates. Most of the transformations are focussed toward the hydroboration of terminal alkynes, but the unsymmetrical functionalised alkynes especially ynamides are not fully explored till date. The most challenging part associated with this kind of transformation is the controlling regio as well as stereoselectivity of the reaction. newlineThe thesis entitled Studies on Cu(I)- catalysed Regio and Stereo- selective Hydroboration of Ynamides is an effort towards understanding the involved catalytic system and the mechanism during regioselective hydroboration of ynamides. It consists of three ma