Computational study of unprecedented palladium-catalyzed amination of chloromethylnaphthalene with pyrrolidine

WANG Qin; JIA Jianfeng; WU Haishun

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Computational study of unprecedented palladium-catalyzed amination of chloromethylnaphthalene with pyrrolidine

WANG Qin,JIA Jianfeng,WU Haishun * #

School of Chemistry and Materials Science, Shanxi Normal University, Linfen 041004

*Correspondence author

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Funding: Work supported by the Natural Science Foundation of China （No.21031003）, the National Basic Research 973 Pre-research Program of China （No.2010CB635110）, the Specialized Research Fund for the Doctoral Program of Higher Education of China（No.20101404110001）

Opened online:10 February 2014

Accepted by: none

Citation: WANG Qin,JIA Jianfeng,WU Haishun.Computational study of unprecedented palladium-catalyzed amination of chloromethylnaphthalene with pyrrolidine[OL]. [10 February 2014] http://en.paper.edu.cn/en_releasepaper/content/4584352

The reductive elimination in the amination reactions of chloromethylnaphthalene with pyrrolidine by Pd(0) complexes have been theoretically studied with the density functional theory. Our studies indicates that there are two possible reaction pathways from the two conformers. Both two pathways involves three major steps: the isomerization from η1-menaphthyl complex to η3-menaphthyl complex, the η3-menaphthyl rearrangement from η3-exo-menaphthyl complex to η3-endo-menaphthyl complex, and migratory insertion of amino-group to naphthyl. On the basis of the DFT calculations, we found that product of amination is ortho-aminated product kinetically and para-aminated product thermodynamically. It is noted that the tetrahydrofuran as solvent does not change the trends of the potential energy surface compared to that found in the gas phase.

Keywords:Density functional theory; Palladadium; Amination; Regioselectivity

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