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Updated: Jan 8, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Copper-Catalyzed Three-Component Radical 1,2-Carboazidation of 1,3-Dienes
Xiaoyan Shangguan1, Yan Li1, Qian Zhang1,2
1Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China.
Abstract:
Organic azides serve as versatile synthons in organic synthesis, owing to their unique reactivity. Although transition-metal-catalyzed radical azidative difunctionalization of alkenes has achieved considerable progress, the analogous transformation of 1,3-dienes, particularly carboazidation, remains underdeveloped. Herein, we report a copper-catalyzed three-component 1,2-carboazidation of 1,3-dienes with TMSN3 and diacyl peroxides. The reaction proceeds under mild conditions with exclusive 1,2-regioselectivity, efficiently affording (E)-allylic azides. This method provides a practical strategy for the synthesis of allylic azides.
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