Issue 5, 2014

Mechanistic understanding of domino cyclization between gem-dialkylthio vinylallenes and benzylamine towards economic synthesis: a computational study

Abstract

DFT investigations are carried out to improve the domino cyclization between gem-dialkylthio vinylallenes and benzylamine. Economic reaction approaches were explored, namely, this reaction can occur under organic solvent-free conditions either catalyzed by trace water or self-catalyzed by BnNH2. Three types of reactions (DMSO-assisted, trace water-catalyzed, and self-catalyzed by BnNH2) shared the same reaction mechanism with the nucleophilic attack of BnNH2 on the allenic carbon of thioamide intermediate Re. For trace water-catalyzed reaction another mechanism was also found that is the BnNH2 attacks the carbonyl carbon of the conformational isomer of Re. Among the investigated mechanisms, the trace water-catalyzed one is suggested to be the most efficient and convenient synthetic method for pyrroles. Our calculated results were further confirmed by the experimental observation, which opens a new strategy for the synthesis of pyrroles.

Graphical abstract: Mechanistic understanding of domino cyclization between gem-dialkylthio vinylallenes and benzylamine towards economic synthesis: a computational study

Supplementary files

Article information

Article type
Paper
Submitted
03 Nov 2013
Accepted
06 Feb 2014
First published
10 Feb 2014

Green Chem., 2014,16, 2653-2663

Mechanistic understanding of domino cyclization between gem-dialkylthio vinylallenes and benzylamine towards economic synthesis: a computational study

H. Yuan, Y. Zheng, Z. Fang, X. Bi and J. Zhang, Green Chem., 2014, 16, 2653 DOI: 10.1039/C3GC42259C

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