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Synfacts 2026; 22(01): 33
DOI: 10.1055/a-2738-9922
Metals in Synthesis

Dual-Ligand Copper-Catalyzed α-Azidation of Amides

Authors

Zhang H, Gu W, Zheng J, Lu J, Li Q, Liu Y, Qi X *, Zhang G *, Guo R *. Wuhan University and Central China Normal University, Wuhan, P. R. China
Ligand Evolution-Enabled Enantioselective C(sp3)–H Azidation.

J. Am. Chem. Soc. 2025;
147: 40010-40023
DOI: 10.1021/jacs.5c16924
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Keywords

copper catalysis - ligand development - asymmetric - azidation

Significance

Guo, Zhang, Qi and co-workers report a novel bisoxazolinediphenylamine (BOPA) ligand for the enantioselective α-azidation of amides. The use of a second phosphine ligand (DPPM) proved to be crucial for reactivity and enantioselectivity in this dual-ligand, copper-catalyzed methodology.


Comment

DFT studies suggested that the incorporation of DPPM resulted in a dual-ligand-ligated copper species which was beneficial for enantiocontrol. The dual-ligated copper species was calculated to have a compressed active site, a major contributor to the observed high enantioselectivity.




Publication History

Article published online:
16 December 2025

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