Issue 18, 2021

Copper-catalyzed domino synthesis of benzo[d]imidazo[5,1-b][1,3]selenazoles involving sequential intermolecular cycloaddition and intramolecular Ullmann-type C–Se bond formation

Abstract

The copper-catalyzed cascade cyclization of 2-haloaryl isoselenocyanates with isocyanides to access benzo[d]imidazo[5,1-b][1,3]selenazoles has been realized efficiently under ligand-free conditions. The less commonly developed isoselenocyanates served as the selenium sources for the preparation of a new class of selenium-containing heterocyclic compounds. This protocol was designed to involve sequential intermolecular [3 + 2] cycloaddition and intramolecular Ullmann-type C–Se bond formation.

Graphical abstract: Copper-catalyzed domino synthesis of benzo[d]imidazo[5,1-b][1,3]selenazoles involving sequential intermolecular cycloaddition and intramolecular Ullmann-type C–Se bond formation

Supplementary files

Article information

Article type
Research Article
Submitted
05 Jun 2021
Accepted
12 Jul 2021
First published
13 Jul 2021

Org. Chem. Front., 2021,8, 5139-5144

Copper-catalyzed domino synthesis of benzo[d]imidazo[5,1-b][1,3]selenazoles involving sequential intermolecular cycloaddition and intramolecular Ullmann-type C–Se bond formation

K. Yan, M. Liu, J. Wen, W. Liu, X. Li, X. Liu, X. Sui, W. Shang and X. Wang, Org. Chem. Front., 2021, 8, 5139 DOI: 10.1039/D1QO00851J

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