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Updated: Sep 10, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Electrochemical [2+2+1] Dimerization Annulation of Styrenes and TMSN3 via Schmidt Rearrangement: Direct Access to
Bin Song1, Pengxiang Gao1, Feng Zhao1
1School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, Jiangsu 210094, China.
Abstract:
A significant advancement has been made in the dimerization and cyclization of styrenes in one step to construct nitrogen-containing heterocyclic skeletons. Herein, we report a novel [2+2+1] dimerization annulation of styrenes and TMSN3 via Schmidt rearrangement, enabling straightforward access to 1-pyrrolines from the most easily available materials. Different from 5-exo-trig cyclization, this strategy not only obviated the needs of an oxidant, a metal, and presynthesis but also possessed simple and green operations. Besides, mechanistic studies indicated a radical pathway was involved, which was further demonstrated by DFT computational analysis. These findings highlight the potential of direct electro-activation of olefins to address the existing challenges in dimerization cyclization of olefins.
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