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

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 yi...

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Published inChemical communications (Cambridge, England) Vol. 59; no. 4; pp. 656 - 659
Main Authors Li, Zhi, Lan, Deyou, Zhou, Wei, Li, Jiacheng, Zhu, Hui, Yu, Chuanming, Jiang, Xinpeng
Format Journal Article
Published 16.05.2023
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Summary: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. Halosulfoamidation of [1.1.1]propellane with sodium hypohalites and sulfonamides provides a sustainable way to synthesize C3-halo substituted bicyclo[1.1.1]pentylamine.
Bibliography:https://doi.org/10.1039/d3cc01262j
Electronic supplementary information (ESI) available. See DOI
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc01262j