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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

Rezensent(en):
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.


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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.


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Publikationsverlauf

Artikel online veröffentlicht:
18. Mai 2021

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