Lü Shiwei, Wang Zipeng, Gao Xiang, Chen Kai, Zhu Shifa
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, 1510640, Guangzhou, China.
College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, China.
Angew Chem Int Ed Engl. 2023 Apr 11;62(16):e202300268. doi: 10.1002/anie.202300268. Epub 2023 Mar 13.
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.
尽管将气态乙炔直接转化为高附加值的液态商品化学品正变得越来越有吸引力，但大多数已有的方法都集中在交叉偶联、氢官能化和聚合反应上。在此，我们描述了一种1,2-双官能化方法，该方法可将乙炔直接插入易于获得的双官能试剂中。这种方法能够以高区域选择性和立体选择性获得各种C2连接的1,2-双杂原子产物，同时开辟了以前未探索的合成方向。此外，我们通过将所得产物转化为各种功能化分子和含手性亚砜的双齿配体，展示了该方法的合成潜力。结合实验和理论方法，对这种插入反应的机理进行了研究。
