Theoretical Studies on The Mechanism of Pd2+-Catalyzed Regioselective C-H Alkylation of Indole With MesICH2CF3OTf
| Autor: | Yao Shi, Hongsheng Ma, Jiaxuan Shao, Chao Deng |
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| Rok vydání: | 2021 |
| Předmět: |
Indole test
Reaction mechanism 010304 chemical physics Metalation Chemistry Organic Chemistry Regioselectivity Alkylation 010402 general chemistry 01 natural sciences Oxidative addition Medicinal chemistry Catalysis Reductive elimination Transition state 0104 chemical sciences Computer Science Applications Inorganic Chemistry Computational Theory and Mathematics 0103 physical sciences Physical and Theoretical Chemistry |
| DOI: | 10.21203/rs.3.rs-194046/v1 |
| Popis: | The reaction mechanism of Pd2+-catalyzed regioselective C–H alkylation of indole with MesICH2CF3OTf has been investigated by the density functional theory calculations. The reaction mechanism mainly contains four steps：C-H activation, oxidative addition, reductive elimination and ligands substitution. From our calculations, we find that the C-H activation step was realized by the acetate anion (-OAc) assisted CMD process and the transition state of C-H activation process is a square planar configuration. Moreover, the calculation results suggest that the regioselectivity of C-H bond alkylation of indole with MesICH2CF3OTf can be ascribed to the different stability of the CMD transition states in C-H activation step and different acidities of C-H bonds. |
| Databáze: | OpenAIRE |
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