A DFT study on the reaction mechanisms of phosphonation of heteroaryl N-oxides with H-phosphonates
作者： Wei Zhang , Xiaoyang Zhao , Yan Qiao , Xiaokang Guo , Yanyan Wang
DOI: 10.1016/J.COMPTC.2015.08.012
关键词:
摘要: Abstract In this paper, a density functional theory (DFT) study has been carried out to theoretically investigate the mechanisms of direct regioselective phosphonation heteroaryl N-oxides ( A ) with H-phosphonates B1 under metal- and external oxidant-free conditions. The calculated results indicate that reaction proceeds through two stages including nucleophilic addition H-phosphonate N-oxide dehydration. Starting from reactant or its tautomer B2 , possible pathways have suggested studied in first stage. Moreover, three channels -assisted dehydration, dehydration investigated compared second Based on computational results, we can conclude both associated are occur experimental condition, / would lower barriers than This work should be helpful for understanding detailed mechanism title reaction, thus provide valuable insights into rational design effective method/condition kind reaction.
elsevier.com
sci-hub.se 参考文章(33)
RD Vargas-Sánchez, AM Mendoza-Wilson, GR Torrescano-Urrutia, A Sánchez-Escalante, None, Antiradical potential of phenolic compounds fingerprints of propolis extracts: DFT approach Computational and Theoretical Chemistry. ,vol. 1066, pp. 7- 13 ,(2015) , 10.1016/J.COMPTC.2015.05.003
Honghong Zhang, A DFT study on direct hydrogenation of amide catalyzed by a PNN Ru(II) pincer complex Computational and Theoretical Chemistry. ,vol. 1066, pp. 1- 6 ,(2015) , 10.1016/J.COMPTC.2015.05.002
Juntian Niu, Jingyu Ran, Ruirui Wang, Xuesen Du, Mechanism of methylene oxidation on Pt catalysts: A DFT study Computational and Theoretical Chemistry. ,vol. 1067, pp. 40- 47 ,(2015) , 10.1016/J.COMPTC.2015.05.022
Yang Wang, Xiaokang Guo, Mingsheng Tang, Donghui Wei, Theoretical Investigations toward the Asymmetric Insertion Reaction of Diazoester with Aldehyde Catalyzed by N-Protonated Chiral Oxazaborolidine: Mechanisms and Stereoselectivity Journal of Physical Chemistry A. ,vol. 119, pp. 8422- 8431 ,(2015) , 10.1021/ACS.JPCA.5B04793
Yuan-qiang Zhu, Hong Su, Junlei Tang, Yaqi Yang, Mechanism of palladium(II)-catalyzed reaction between styrene and carbazole Computational and Theoretical Chemistry. ,vol. 1068, pp. 47- 51 ,(2015) , 10.1016/J.COMPTC.2015.06.010
Shijun Li, Huabiao Tang, Yang Wang, Yanyan Zhu, De-Cai Fang, Donghui Wei, Mingsheng Tang, A DFT study on the competing mechanisms of PPh3-catalyzed (3 + 3) and (3 + 2) annulations between 5-acetoxypenta-2,3-dienoate and 1C,3O-bisnucleophiles Journal of Molecular Catalysis A-chemical. ,vol. 407, pp. 137- 146 ,(2015) , 10.1016/J.MOLCATA.2015.06.032
Donghui Wei, Mingsheng Tang, Chang-Guo Zhan, Fundamental reaction pathway and free energy profile of proteasome inhibition by syringolin A (SylA) Organic and Biomolecular Chemistry. ,vol. 13, pp. 6857- 6865 ,(2015) , 10.1039/C5OB00737B
Yanyan Wang, Yang Wang, Wenjing Zhang, Yanyan Zhu, Donghui Wei, Mingsheng Tang, Mechanisms and stereoselectivities of the Rh(I)-catalyzed carbenoid carbon insertion reaction of benzocyclobutenol with diazoester. Organic and Biomolecular Chemistry. ,vol. 13, pp. 6587- 6597 ,(2015) , 10.1039/C5OB00608B
Yunxia Li, Yanyan Zhu, Wenjing Zhang, Donghui Wei, Yingying Ran, Qilin Zhao, Mingsheng Tang, A DFT study on the reaction mechanism of dimerization of methyl methacrylate catalyzed by N-heterocyclic carbene. Physical Chemistry Chemical Physics. ,vol. 16, pp. 20001- 20008 ,(2014) , 10.1039/C4CP02186J
Yang Wang, Donghui Wei, Wenjing Zhang, Yanyan Wang, Yanyan Zhu, Yu Jia, Mingsheng Tang, A theoretical study on the mechanisms of the reactions between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles. Organic and Biomolecular Chemistry. ,vol. 12, pp. 7503- 7514 ,(2014) , 10.1039/C4OB01015A