Halogen Bond Catalysis on Carbonyl-Olefin Ring-Closing Metathesis Reaction:Comparison with Lewis Acid Catalysis  

作　　者：Ying Li Yuanyuan Sun Lingpeng Meng Qingzhong Li Yanli Zeng 

机构地区：[1]College of Chemistry and Materials Science,Hebei Key Laboratory of Inorganic Nano-materials,Hebei Normal University,Shijiazhuang,Hebei 050024,China [2]The Laboratory of Theoretical and Computational Chemistry,College of Chemistry&Chemical Engineering,Yantai University,Yantai,Shandong 264005,China

出　　处：《Chinese Journal of Chemistry》2022年第11期1275-1284,共10页中国化学（英文版）

基　　金：This work was supported by the Natural Science Foundation of Hebei Province(B2019205113,B2019205061);the National Natural Science Foundation of China(21973025);the Science Foundation of Hebei Normal University(L2020Z04).

摘　　要：The carbonyl-olefin ring-closing metathesis reactions have become a powerful tool for carbon-carbon bond formation.In this work,the halogen bond catalysis and classical Lewis acid catalysis on the carbonyl-olefin ring-closing metathesis reaction were investigated by density function theory.For both the halogen bond catalysis and classical Lewis acid catalysis,the carbonyl-olefin ring-closing me-tathesis reaction occurs by[2+2]-cycloaddition process and[2+2]-cycloreversion process,the reaction energy barriers are low,there-fore,it can be performed easily at room temperature.The essential difference of the two kinds of catalysts is that the catalytic mecha-nism of halogen bond catalysis is mainly contribution of electrostatic interaction,while that of classical Lewis acid catalysis is mainly catalyzed by orbital interaction.The halogen bond donor catalysts(ICI_(3),IF_(3))are expected to be efficient catalysts for the reaction and further promote the chemical synthesis of carbonyl-olefin ring-closing metathesis reaction.

关 键 词：Halogen bond donors Lewis acids Electrostatic interactions Orbital interaction Carbonyl-olefin ring-closing metathesis 

分 类 号：O64[理学—物理化学]