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DFT Investigation for the Mechanisms of Csp3-H Functionalization of Glycine Derivatives Induced by Radical Cation Salt

Abstract

The mechanisms for the reaction between ethyl 2-(p-tolylamino)acetate and phenylethylene have been investigated using M06-L-D3/6-311+G(d,p) level, and the SMD model was applied to simulate the solvent. The computational results suggest that the Csp3-H functionalization of ethyl 2-(p-tolylamino)acetate has two possible paths; then there are three probable paths (I, II or III) to yield the final product. In path I, one D-A addition reaction could produce the product compound; finally the oxidative dehydrogenation could yield the product with the assistance of O2. The additive InCl3 can accelerate the D-A reaction via four possible paths, and the NOFF, FMOT and Fukui function can be applied to analyze the D-A reaction; while in path II and III, the formed radical intermediate would go through a series of addition reaction, oxidation reaction, ring-closure reaction and oxidative dehydrogenation to yield the final product. The results could provide valuable insights into these types of interactions and related ones.

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Article information


Submitted
30 Jul 2019
Accepted
29 Dec 2019
First published
30 Dec 2019

New J. Chem., 2020, Accepted Manuscript
Article type
Paper

DFT Investigation for the Mechanisms of Csp3-H Functionalization of Glycine Derivatives Induced by Radical Cation Salt

D. Zhou and P. Wang, New J. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9NJ03946E

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