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Synfacts 2021; 17(06): 0641
DOI: 10.1055/s-0040-1720648
Metals in Synthesis

Synthesis of Hydrazides by N–N Coupling

Contributor(s):
Mark Lautens
,
Joachim Loup
Wang H, Jung H, Song F, Zhu S, Bai Z, Chen D, He G, Chang S, *, Chen G. * Nankai University, Tianjin, P. R. of China; Korea Advanced Institute of Science and Technology (KAIST) and Institute for Basic Science (IBS), Daejeon, Republic of Korea
Nitrene-Mediated Intermolecular N–N Coupling for Efficient Synthesis of Hydrazides.

Nat. Chem. 2021;
13: 378-385
DOI: 10.1038/s41557-021-00650-0
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Key words

iridium catalysis - iron catalysis - hydrazides - nitrenes

Significance

Chang, Chen, and co-workers report a synthesis of hydrazides from arylalkylamines and dioxazolones, which serve as nitrene precursors. Iridium complexes as well as simple iron halides were found to efficiently catalyze the transformation.


 

Comment

The reaction proceeds under mild conditions with excellent functional group tolerance, including pseudopeptides. Mechanistic studies indicate that the attack of the electrophilic iridium-nitrenoid intermediate by the amine is assisted by Cl···HN bonding.


 

 

Publication History

Article published online:
18 May 2021

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