Intramolecular α-oxygenation of amines via n-heterocyclic carbene-catalyzed domino reaction of aryl aldehyde: Experiment and dft calculation

14Citations
Citations of this article
6Readers
Mendeley users who have this article in their library.

Abstract

We have developed an N-heterocyclic carbene (NHC)-catalyzed domino reaction with aryl aldehyde through a simple acyl azolium intermediate using phenyliodine(III) diacetate (PIDA) as an oxidant. Controlled experiments and density functional theory calculations supported a domino two-stage mechanism from aldehyde/amine to an α-oxygenation product, including NHC-catalyzed oxidation of the aldehyde to carboxylic acid via acyl azolium intermediate, and further, an addition of carboxylate to iminium intermediate. Our study reveals a new model for the oxidation of Breslow intermediate via electrophilic attack of the hydroxyl group by PIDA.

References Powered by Scopus

Catalytic dehydrogenative cross-coupling: Forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds

3587Citations
N/AReaders
Get full text

An overview of N-heterocyclic carbenes

3447Citations
N/AReaders
Get full text

Organocatalysis by N-heterocyclic carbenes

2720Citations
N/AReaders
Get full text

Cited by Powered by Scopus

N-Heterocyclic carbene/photo-cocatalyzed oxidative Smiles rearrangement: Synthesis of aryl salicylates from: O -aryl salicylaldehydes

61Citations
N/AReaders
Get full text

Oxidative N-Heterocyclic Carbene Catalysis

37Citations
N/AReaders
Get full text

N-Heterocyclic Carbene Catalyzed Photooxidation: Intramolecular Cross Dehydrogenative Coupling of Tetrahydroisoquinoline-Tethered Aldehydes

26Citations
N/AReaders
Get full text

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Cite

CITATION STYLE

APA

Chen, X. Y., Zhang, C. S., Yi, L., Gao, Z. H., Wang, Z. X., & Ye, S. (2019). Intramolecular α-oxygenation of amines via n-heterocyclic carbene-catalyzed domino reaction of aryl aldehyde: Experiment and dft calculation. CCS Chemistry, 1(4), 343–351. https://doi.org/10.31635/ccschem.019.20190020

Readers' Seniority

Tooltip

Professor / Associate Prof. 1

50%

PhD / Post grad / Masters / Doc 1

50%

Readers' Discipline

Tooltip

Environmental Science 1

50%

Chemistry 1

50%

Save time finding and organizing research with Mendeley

Sign up for free