Issue 18, 2020

Dimerization–cyclization reactions of isocyanoaryl-tethered alkylidenecyclobutanes via a triplet biradical mediated process

Abstract

A triplet biradical mediated dimerization–cyclization reaction of isocyanoaryl-tethered alkylidenecyclobutanes has been reported in this paper, giving a new protocol for the construction of macrocyclic skeletons including dihydroquinoline and quinoline units in moderate yields. The reaction proceeded through a key 1,4-diazabutatriene intermediate along with intramolecular redox to produce a biradical intermediate species, which subsequently experienced bond-breaking and -making processes to give the desired product. The reaction mechanism was supported by density functional theory (DFT) calculations.

Graphical abstract: Dimerization–cyclization reactions of isocyanoaryl-tethered alkylidenecyclobutanes via a triplet biradical mediated process

Supplementary files

Article information

Article type
Research Article
Submitted
23 জুলাই 2020
Accepted
30 জুলাই 2020
First published
31 জুলাই 2020

Org. Chem. Front., 2020,7, 2634-2643

Dimerization–cyclization reactions of isocyanoaryl-tethered alkylidenecyclobutanes via a triplet biradical mediated process

L. Tao, Y. Wei and M. Shi, Org. Chem. Front., 2020, 7, 2634 DOI: 10.1039/D0QO00878H

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