The first example of a click reaction with a carboranyl azide and an olefin

TETRAHEDRON

卷:75

Article

Chauhan, Uday B.¹  Tomich, Anton W.¹  Lavallo, Vincent¹ 

[1] Univ Calif Riverside, Dept Chem, 501 Big Springs Rd, Riverside, CA 92521 USA

关键词: Carboranes;    Click chemistry;    Metal-free click;    Heterocycles;    Triazoline;   

DOI  :  10.1016/j.tet.2019.01.049

来源: Elsevier

【 摘 要 】

While typical organic azides have long been known to undergo 1-3 dipolar cycloadditions with strained C-C multiple bonds, such chemistry has never been reported between organomimetic carboranyl azides and alkenes. Here we show that the carborane o-PhCN3CB10H10 readily undergoes cycloaddition with norbornene at ambient temperature to afford the corresponding triazole adduct with perfect exo-selectivity. The structure of the ensuing heterocycle was unambiguously determined by multinuclear NMR, correlation NMR, and single crystal X-ray diffraction experiments. This first example of such reactivity demonstrates a method to easily introduce carborane clusters directly to scaffolds of interest, without having an organic spacer between the azide functionality and cluster. (C) 2019 Published by Elsevier Ltd.

【 授权许可】

Free