DFT study on the C(sp3)-H Silylation of N-benzyl-N-ethylethanamine catalyzed by B(C6F5)3

2025-09-01

PRE

Zhong, Lu-jia

Tiantian Feng

Qin Xiao

周

周大刚 (Da‐Gang Zhou)

杨

杨丽君 (Lijun Yang) *

DOI：10.1016/j.chemphys.2025.112935

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The mechanisms for the Csp3-H silylation of N-benzyl-N-ethylethanamine have been investigated by employing the M06-2x-D3/ma-def2-TZVP level. The SMD method, based on solute electron density, was used to simulate the solvent of p-xylene. Computational results reveal that B(C6F5)3 as the catalyst can help to finish the Csp3-H activation; moreover, B(C6F5)3 and N-benzyl-N-ethylethanamine can complete the conversion from N-benzyl-Nethylethanamine to alkene derivative, which can reacts with the protonated diphenylsilane to get the adding intermediate. Finally, there are two paths (a and b) that could yield the final product the 1-benzyl-4,4-diphenyl1,4-azasilinane. The Gibbs free energy profile concludes that path b2 with lower energy barrier is optimal. The calculations could provide valuable insights for understanding similar reactions and developing new C(sp3)-H silylation.

Keywords:

DFT

N -benzyl

N -ethylethanamine

Csp3-H Silylation

DFT study on the C(sp3)-H Silylation of N-benzyl-N-ethylethanamine catalyzed by B(C6F5)3

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