Although the direct conversion of gaseous acetylene into value-added liquid commodity chemicals is becoming increasingly attractive, the majority of the established methodologies are focused on cross-coupling, hydro-functionalization, and polymerization. Herein, we describe a 1,2-difunctionalization method that inserts acetylene directly into readily available bifunctional reagents. This method provides access to diverse C2-linked 1,2-bis-heteroatom products in high regio- and stereoselectivity along with opening up previously unexplored synthetic directions. In addition, we demonstrate this method's synthetic potential by converting the obtained products into diverse functionalized molecules and chiral sulfoxide-containing bidentate ligands. Using a combination of experimental and theoretical methods, the mechanism for this insertion reaction was investigated.
Keywords: 1,2-Difunctionalization; Acetylene; Olefins; Photochemistry; Radical Chemistry.
© 2023 Wiley-VCH GmbH.