SYNTHESIS OF 2-PHENYLBUTYN-3-OLA-2 BASED ON ENANTIOSELECTIVE ALKYNYLATION OF ACETOPHENONE AND ITS CHEMICAL MODIFICATIONS

Abstract

In this study, the synthesis of 2-phenylbut-3-yn-2-ol through the enantioselective alkynylation reaction of acetophenone in a 3,3′-Ph2BINOL-2Li/Ti(OiPr)4/Et2Zn complex catalytic system was investigated, along with its oxidation-driven homolytic coupling and Sonogashira cross-coupling reactions with benzyl chloride. Various factors influencing the synthesis process and the yield of acetylene diol products have been systematically studied - temperature, reaction duration, nature of catalysts and solvents, amounts of reagents and substrates, types and amounts of intermediates and by-products formed in the reaction. Based on the results obtained, the most optimal conditions for the nucleophilic coupling process were determined and reaction mechanisms were proposed. The synthesized product have been identified, and their partial constants, structure, purity and composition have been proven using modern physicochemical methods.