Tale of the Breslow intermediate, a central player in N-heterocyclic carbene organocatalysis: then and now

M Pareek, Y Reddi, RB Sunoj - Chemical Science, 2021 - pubs.rsc.org
N-Heterocyclic carbenes (NHCs) belong to the popular family of organocatalysts used in a
wide range of reactions, including that for the synthesis of complex natural products and …

Recent Advances on Computational Investigations of N‐Heterocyclic Carbene Catalyzed Cycloaddition/Annulation Reactions: Mechanism and Origin of Selectivities

Y Wang, D Wei, W Zhang - ChemCatChem, 2018 - Wiley Online Library
The developments of theoretical studies on NHC‐catalyzed [n+ 2](n= 2, 3, 4) and other
cycloaddition/annulation reactions have been summarized in this review. The detailed …

Exploring a general mechanistic map on NHC-catalyzed activation/transformation reactions of saturated carboxylic anhydrides

SL Liu, Y Qiao, Y Wang - Organic Chemistry Frontiers, 2023 - pubs.rsc.org
A general mechanistic map involving multiple intermediates and pathways has been
proposed and systematically studied for NHC-catalyzed transformation reactions of …

Multiple functional organocatalyst-promoted inert C–C activation: Mechanism and origin of selectivities

M Zhang, Y Wang, SJ Li, X Wang, Q Shi, X Li… - ACS …, 2021 - ACS Publications
Although breakthroughs in the N-heterocyclic carbene (NHC)-catalyzed inert C–C bond
activation strategy have been achieved, understanding the role of the catalyst as well as the …

N-Heterocyclic Carbene (NHC)-Catalyzed sp3 β-C–H Activation of Saturated Carbonyl Compounds: Mechanism, Role of NHC, and Origin of Stereoselectivity

Y Wang, D Wei, Y Wang, W Zhang, M Tang - ACS Catalysis, 2016 - ACS Publications
Activation of inert sp3 β-C–H bonds has attracted widespread attention and been developed
with significant progress in recent years, but understanding the mechanism of this kind of …

Origin of stereoselectivity in cooperative asymmetric catalysis involving N-heterocyclic carbenes and lewis acids toward the synthesis of spirooxindole lactone

Y Reddi, RB Sunoj - ACS Catalysis, 2017 - ACS Publications
An increasing number of examples are now being reported that use chiral N-heterocyclic
carbenes (NHCs) in conjunction with Lewis acids to enhance catalytic potential. Herein, we …

Prediction of NHC-catalyzed chemoselective functionalizations of carbonyl compounds: a general mechanistic map

X Li, J Xu, SJ Li, LB Qu, Z Li, YR Chi, D Wei, Y Lan - Chemical Science, 2020 - pubs.rsc.org
Generally, N-heterocyclic carbene (NHC) complexed with carbonyl compounds would
transform into several important active intermediates, ie, enolates, Breslow intermediates, or …

Harnessing noncovalent interactions in dual-catalytic enantioselective Heck–Matsuda arylation

Y Reddi, CC Tsai, CM Avila, FD Toste… - Journal of the American …, 2018 - ACS Publications
The use of more than one catalyst in one-pot reaction conditions has become a rapidly
evolving protocol in the development of asymmetric catalysis. The lack of molecular insights …

Insights into the N-Heterocyclic Carbene (NHC)-Catalyzed Oxidative γ-C(sp3)–H Deprotonation of Alkylenals and Cascade [4 + 2] Cycloaddition with …

X Li, Y Wang, Y Wang, M Tang, LB Qu… - The Journal of Organic …, 2018 - ACS Publications
The N-heterocyclic carbene (NHC)-catalyzed oxidative C–H deprotonations have attracted
increasing attention; however, the general mechanism regarding this kind of oxidative …

Computational study on γ-C–H functionalization of α, β-unsaturated ester catalyzed by N-heterocyclic carbene: Mechanisms, origin of stereoselectivity, and role of …

Y Wang, D Wei, M Tang - The Journal of Organic Chemistry, 2017 - ACS Publications
The N-heterocyclic carbene (NHC)-catalyzed γ-C–H deprotonation/functionalization of α, β-
unsaturated esters with hydrazones leading to the δ-lactams has been theoretically …