Issue 40, 2023

Synthesis of C3-halo substituted bicyclo[1.1.1]pentylamines via halosulfoamidation of [1.1.1]propellane with sodium hypohalites and sulfonamides

Abstract

Herein, we report a catalyst-free synthesis of C3-halo substituted bicyclo[1.1.1]pentylamines under mild conditions. The reaction involves the use of sodium hypohalites and sulfonamides to generate N-halosulfonamides in situ, which subsequently undergo radical addition with [1.1.1]propellane to yield the desired products with suitable functional group tolerance.

Graphical abstract: Synthesis of C3-halo substituted bicyclo[1.1.1]pentylamines via halosulfoamidation of [1.1.1]propellane with sodium hypohalites and sulfonamides

Supplementary files

Article information

Article type
Communication
Submitted
14 Mar 2023
Accepted
11 Apr 2023
First published
12 Apr 2023

Chem. Commun., 2023,59, 6056-6059

Synthesis of C3-halo substituted bicyclo[1.1.1]pentylamines via halosulfoamidation of [1.1.1]propellane with sodium hypohalites and sulfonamides

Z. Li, D. Lan, W. Zhou, J. Li, H. Zhu, C. Yu and X. Jiang, Chem. Commun., 2023, 59, 6056 DOI: 10.1039/D3CC01262J

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