N=N Homocoupling of Alkyl Azides: Cobalt-Catalyzed Synthesis of Azoalkanes

Keywords

azides - cobalt catalysis - azoalkanes - bimetallic catalysis

Significance

Uyeda and co-workers report a homobimetallic cobalt catalyst which enacts denitrogenative dimerization of tertiary alkyl azides to form symmetric azoalkanes. The resulting azoalkanes undergo efficient radical generation upon heating or exposure to photocatalysts, making them useful synthetic intermediates.

 

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Comment

The isostructural Ni-catalyst to [Co₂] that the Uyeda group previously reported for the dimerization of aryl azides (J. Am. Chem. Soc. 2018, 140, 4110) was poorly selective for the dimerization of adamantyl azide due to competitive HAT. The authors propose that this is due to two fewer electrons in the [Co₂] complex which prevents the formation of imidyl radical complex responsible for HAT.

 

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Publication History

Article published online:
23 September 2025