Selective Aerobic C-H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles.

doi:10.1021/acs.orglett.7b01061

Paper

Selective Aerobic C-H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles.

Published May 17, 2017 · Long Liu, Liang-Wei Qian, Shaofeng Wu

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22

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Abstract

Using O2 as the oxidant, the benzoxazole frameworks can be directly constructed from the readily available phenols and primary amines in the presence of NH4PF6 over copper under mild conditions. Mechanistic studies showed that a novel mechanism involving biphenyldiols and o-quinones very possibly takes effect in the reaction, because both can selectively give the benzoxazoles under the reaction conditions. An unprecedented unstrained Caryl-Caryl bond cleavage takes place in the reaction.

Study Snapshot

This study demonstrates a novel method for selectively constructing benzoxazole frameworks from readily available phenols and primary amines over copper, potentially involving biphenyldiols and o-quinones.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Selective Aerobic C-H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles.

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References

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Recent methodologies exploiting C-C single-bond cleavage of strained ring systems by transition metal complexes show promise for efficient synthesis of complex organic compounds.

Citations

Metal-Free Oxidative Annulation of Phenols and Amines: A General Synthesis of Benzoxazoles.

This metal-free synthesis of benzoxazoles from abundant phenols and amines offers advantages in generality, selectivity, efficiency, and atom- and step-economies compared to traditional methods.

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Cu-catalyzed synthesis of benzoxazoles from phenols and cyclic oxime esters allows for large-scale syntheses of Ezutromid and Flunoxaprofe in one or two steps.

Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: a combined experimental and computational study

This study developed an efficient metal-free rearrangement reaction for the construction of ortho-sulfonamide phenols, offering mild conditions, broad functional group compatibility, and good regioselectivity.

2-Aryl-perfluorobenzoxazoles: synthesis, fluorescence properties and synthetic applications in cubic platinum nanoparticles

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[3+1+1] Annulation Reaction of Benzo‐1,2‐Quinones, Aldehydes and Hydroxylamine Hydrochloride: Access to Benzoxazoles with Inorganic Nitrogen Source

Inorganic hydroxylamine hydrochloride can efficiently synthesize useful benzoxazoles in high yields, with quinone oxime as the reaction intermediate.

Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides.

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