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Ni-Catalyzed Synthesis of Trisubstituted Hydrazones via Cascade Dehydrogenative Coupling of Alcohol
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DOI：10.1021/acs.joc.6c00096.png)
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Abstract
En 中文
Trisubstituted hydrazones are important motifs in medicinal chemistry and organic synthesis, but conventional methods often require multistep sequences and stoichiometric reagents. In this report, a phosphine-free, air-stable Ni(II)-catalyzed approach is utilized for the acceptorless dehydrogenative coupling of hydrazines, alcohols, and halides for the efficient synthesis of trisubstituted hydrazones. The method proceeds via a tandem sequence under mild conditions, generating only H-2 and H2O as byproducts. This sustainable approach enables direct C-N bond formation from readily available feedstocks with high selectivity and atom economy. We also detected two potential intermediates in the catalytic cycle using an ESI-MS analysis. Based on these studies and control experiments, a catalytic mechanism was proposed. The synthetic utility of the hydrazones is demonstrated by their transformation into Fischer indole, benzimidazole derivatives, and the one-pot synthesis of optodynamer precursors. CHEM21 green metrics indicate that nickel-catalyzed C-N coupling is highly efficient and atom-economic.
Keywords:
ALDEHYDE PHENYLHYDRAZONES
1-ARYL-1H-INDAZOLES
INHIBITORS
STRATEGY
DESIGN
IMINES
AZINES
KETONE
Journal
IF:
3.6
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5.4W
Citations:
8.8W
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