Facile azide formation via diazotransfer reaction in a copper tube flow reactor

TETRAHEDRON LETTERS

卷:56

Article

Nuyts, Koen¹  Ceulemans, Matthias¹  Parac-Vogt, Tatjana N.¹  Bultynck, Geert²  De Borggraeve, Wim M.¹ 

[1] Univ Louvain, KU Leuven, Mol Design & Synth, B-3001 Louvain, Belgium

[2] Univ Louvain, KU Leuven, Lab Mol & Cellular Signaling, B-3001 Louvain, Belgium

关键词: Diazotransfer reaction;    Flow chemistry;    Azides;    Copper reactor;   

DOI  :  10.1016/j.tetlet.2015.02.036

来源: Elsevier

【 摘 要 】

A copper tube flow reactor is used in the conversion of primary amines into organic azides using imidazole-1-sulfonyl azide hydrogen sulfate. The catalyst is generated in situ from the metallic copper. The reaction can be quenched in acidic environment or via a cycloaddition of the azides formed with an alkyne. The possibility to perform this azide-alkyne cycloaddition using the copper released from the reactor is demonstrated with the synthesis of both a 1,2,3-triazole derivative of benzylamine and of a more complex BODIPY-DOTA adduct. (C) 2015 The Authors. Published by Elsevier Ltd.

【 授权许可】

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