Executive Summary : | The importance of Lego-type boron-containing building blocks for automated synthesis of complex small molecules with applications in pharmaceuticals and agrochemicals has been highlighted. The synthesis of literature known building blocks involve multiple steps, whereas the proposed mono- and diboron building blocks could be achieved in one or two steps from easily available starting materials. Here, we use conjugated and skipped diynes for the controlled hydroboration to achieve boron-containing unsaturated compounds. The proposed objective provides easy access to at least four different types of Lego building blocks, which could be directly used in the automated synthesis of various complex targets. With conjugated diynes, we envisage the formation of borylated enynes and conjugated dienes. However, with skipped diynes, independent hydroboration of alkynes could provide borylated skipped enyne and dienes. We also proposed the demonstration of products' capability to undergo iterative SMC reactions. Additionally, a challenging desymmetrization of pro-chiral diynes with hydroboration is proposed to provide chiral borylated skipped enynes and dienes. These methods will bridge the existing bottleneck and the challenges in accessing the organoboron building blocks and facilitate automated synthesis. |