A copper-catalyzed reaction of oximes with diisopropyl azodicarboxylate: an alternative method for the synthesis of oxime carbonates.

doi:10.1039/c6ob02627c

Paper

A copper-catalyzed reaction of oximes with diisopropyl azodicarboxylate: an alternative method for the synthesis of oxime carbonates.

Published Feb 1, 2017 · Muhammad Usman, Zhihui Ren, Yaoyu Wang

Organic & biomolecular chemistry

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Abstract

A new Cu-catalyzed efficient protocol is described for the transformation of oximes to the corresponding carbonate derivatives. Diisopropyl azodicarboxylate acted as a selective new precursor for the synthesis of oxime carbonates in high yields. The O-H bond cleavage and O-C bond formation occur in the presence of a copper catalyst providing a synthetically useful process, which tolerates a wide range of functional groups.

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Copper-catalyzed reaction of oximes with diisopropyl azodicarboxylate effectively synthesizes oxime carbonates in high yields, with wide functional group tolerance.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

A copper-catalyzed reaction of oximes with diisopropyl azodicarboxylate: an alternative method for the synthesis of oxime carbonates.

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References

Synthesis of symmetrical pyridines by iron-catalyzed cyclization of ketoxime acetates and aldehydes

This iron-catalyzed cyclization of ketoxime acetates and aldehydes effectively synthesizes 2,4,6-triarylsubstituted symmetrical pyridines in high yields without additives, demonstrating its scale-up applicability.

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Copper-catalyzed carbonylation of anilines by diisopropyl azodicarboxylate (DIAD) effectively synthesizes various carbamates under solvent-free conditions, offering a promising method for the synthesis of organic compounds.

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This study developed a novel, efficient approach for carbonylating benzamides using Co(OAc)24H2O as a catalyst and azodicarboxylates as a nontoxic carbonyl source, enabling the production of diverse functional groups with ease.

C–H bond activation in the total syntheses of natural products

Transition metal-mediated C-H bond activation is a powerful and ideal method for rapid syntheses of complex natural products and pharmaceuticals.

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This iron-catalyzed cyclization of ketoxime carboxylates and N,N-dialkylanilines efficiently synthesizes diverse pyridines in good to high yields under mild conditions, using readily available starting materials.

Citations

Copper-catalyzed stereoselective alkylhydrazination of alkynes.

Copper-catalyzed stereoselective alkylhydrazination of alkynes provides direct access to tri-substituted (E)-alkenyl-hydrazines with good regio- and stereoselectivity under mild conditions, making it a promising method for

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This Pd(ii)-catalyzed synthesis of quinolin-2(1H)-ones from quinoline N-oxides demonstrates the unexpected reactivity of azodicarboxylates as activating agents and oxidants, allowing for mild conditions and no protection against

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Metal-involving reactions of oximes have advanced in recent years, leading to diverse syntheses and functionalizations of organic species, with potential applications in various fields of chemistry.