The mechanism and impact of mono/bis(iodoimidazolium) halogen bond donor catalysts on Michael addition of indole with trans-crotonophenone: DFT calculations

文献情報

出版日 2022-02-18

DOI 10.1039/D2CP00075J

インパクトファクター 3.676

著者

Yuanyuan Sun, Ying Li, Xiaoyan Li, Yanli Zeng

原文を見る

要旨

Bidentate halogen bond donor catalysts in organic reactions have attracted great attention in recent years. In this work, the catalytic mechanism of mono/bis(iodoimidazolium) halogen bond donor catalysts in the Michael addition reaction is investigated and bis(iodoimidazolium) halogen bond donor catalysts show a good catalytic performance. Catalyzed by these bidentate catalysts, the studied reaction can occur under mild conditions. The whole catalyzed reaction contains two steps. The formation of a carbon–carbon bond in the first step is a nucleophilic reaction of a C-nucleophile. The following proton transfer process contains two possible reaction pathways. Compared to the direct transfer pathway, the pathway of indirect hydrogen proton transfer has a lower energy barrier, and it is more prone to occur. The halogen bond donor catalysts increase the charge transfer of LP(O) → BD*(C–I), thereby accelerating the charge transfer during the formation of the C–C bond and reducing the reaction energy barrier.

掲載誌

Physical Chemistry Chemical Physics

CiteScore: 5.5

自己引用率: 10.3%

年間論文数: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.