The Mechanism of N‐Heterocyclic Carbene Organocatalysis through a Magnifying Glass

O Hollóczki - Chemistry–A European Journal, 2020 - Wiley Online Library
The term “N‐Heterocyclic carbene organocatalysis” is often invoked in organic synthesis for
reactions that are catalyzed by different azolium salts in the presence of bases. Although the …

Charge‐Tagged N‐Heterocyclic Carbenes (NHCs): Revealing the Hidden Side of NHC‐Catalysed Reactions through Electrospray Ionization Mass Spectrometry

C Salvitti, I Chiarotto, F Pepi, A Troiani - ChemPlusChem, 2021 - Wiley Online Library
N‐heterocyclic carbenes (NHCs) are key intermediates in a variety of chemical reactions.
Owing to their transient nature, the interception and characterization of these reactive …

Formation, Oxidation, and Fate of the Breslow Intermediate in the N-Heterocyclic Carbene-Catalyzed Aerobic Oxidation of Aldehydes

O Bortolini, C Chiappe, M Fogagnolo… - The Journal of …, 2017 - ACS Publications
The reaction paths and intermediate structures related to the formation of the Breslow
intermediate and its oxidation along the oxidative/oxygenative lanes have been studied from …

Breslow Intermediates (Amino Enols) and Their Keto Tautomers: First Gas‐Phase Characterization by IR Ion Spectroscopy

M Paul, K Peckelsen, T Thomulka… - … A European Journal, 2021 - Wiley Online Library
Breslow intermediates (BIs) are the crucial nucleophilic amino enol intermediates formed
from electrophilic aldehydes in the course of N‐heterocyclic carbene (NHC)‐catalyzed …

N‐Heterocyclic Carbene Organocatalysis: With or Without Carbenes?

S Gehrke, O Hollóczki - Chemistry–A European Journal, 2020 - Wiley Online Library
In this work the mechanism of the aldehyde umpolung reactions, catalyzed by azolium
cations in the presence of bases, was studied through computational methods. Next to the …

An electrospray-active N-heterocyclic carbene ligand for real-time analysis of organometallic reactions

C Killeen, AG Oliver, JS McIndoe - Dalton Transactions, 2025 - pubs.rsc.org
A charge-tagged N-heterocyclic carbene (NHC) has been synthesized and its utility in
allowing the dynamic behaviour of metal complexes to be monitored in real time using …

Gas Phase Studies of N-Heterocyclic Carbene-Catalyzed Condensation Reactions

Y Tian, JK Lee - The Journal of Organic Chemistry, 2015 - ACS Publications
N-Heterocyclic carbenes (NHCs) catalyze Umpolung condensation reactions of carbonyl
compounds, including the Stetter reaction. These types of reactions have not heretofore …

Probing the gas-phase structure of charge-tagged intermediates of a proline catalyzed aldol reaction–vibrational spectroscopy distinguishes oxazolidinone from …

JA Willms, J Vidic, J Barthelmes, V Steinmetz… - Physical Chemistry …, 2019 - pubs.rsc.org
An L-proline based catalyst with a charged phenyl-pyridium substituent (1) was used to
analyze intermediates of an organocatalyzed aldol reaction by infrared multi-photon …

E-Selective N-heterocyclic carbene-catalyzed reaction of aldehydes and butadienoates: effect of water and chloroform as the proton shuttle

D Ma, Y Song, C Fu, F Zhang, Y Guo… - Organic Chemistry …, 2018 - pubs.rsc.org
As we know, there are many reports on the reactions of the Breslow intermediate with
electron-deficient alkenes or alkynes. However, the reactions with allenes are much less …