A computational reinvestigation of the formation of N-alkylpyrroles via intermolecular redox amination.
A detailed mechanism of N-alkylpyrrole formation from 3-pyrroline and 2-phenylpropanal in the presence of a Brønsted acid catalyst was investigated in depth using the MP2 and DFT theories. The two mechanisms proposed earlier in recent literatures for this internal redox process were evaluated and were found not to account perfectly for the transition state and the energetic barrier of its formation. Based on the present calculations, a new mechanism was put forth.
State Key Laboratory of Elemento-Ogranic Chemistry, Nankai University, Tianjin 300071, China.
Xiaosong
X
Xue
Ao
A
Yu
Yu
Y
Cai
Jin-Pei
JP
Cheng