1,2-Difunctionalization of Acetylene Enabled by Light

作者:Lu, Shiwei; Wang, Zipeng; Gao, Xiang; Chen, Kai*; Zhu, Shifa*
来源:Angewandte Chemie - International Edition, 2023, 62(16).
DOI:10.1002/anie.202300268

摘要

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.