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As a significant variant of the Michael reaction, the 1,6-addition reaction has undergone considerable development over the past decade. This effective strategy enables the synthesis of a variety of novel and potentially bioactive functional molecules. In this review, we summarize the recent progress in NHC-catalyzed 1,6-addition reactions, highlighting their efficiency in the rapid synthesis of complex functional molecules. We also provide our perspectives on the future development of this dynamic and highly active research area.
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http://dx.doi.org/10.1002/tcr.202400125 | DOI Listing |
Org Lett
June 2025
State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
In N-heterocyclic carbene (NHC) catalysis, the reduction of NHC-bound acyl azolium species is achieved with progress limited to the generation of ketyl radical intermediates. Here, we report a novel NHC-catalyzed reductive mode for acyl azolium intermediates, which accept a hydride to generate the Breslow intermediate. Then, the reaction of the Breslow intermediate with chalcone results in the formation of cyclopentene, demonstrating a classic umpolung transformation.
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April 2025
State Key Laboratory of Green Pesticide, Guizhou University, Huaxi District, Guiyang 550025, China.
We summarize in this review the recent key progress in the NHC-catalyzed electrophilic activation of carbonyl compounds for the regioselective functionalization of saccharides, enantioselective construction of heterocycles, and asymmetric synthesis of axially and planar chiral molecules.
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November 2024
College of Chemistry and Chemical Engineering, Guizhou University of Engineering Science, Xueyuan Road, Qixingguan District, Bijie, 551700, China.
As a significant variant of the Michael reaction, the 1,6-addition reaction has undergone considerable development over the past decade. This effective strategy enables the synthesis of a variety of novel and potentially bioactive functional molecules. In this review, we summarize the recent progress in NHC-catalyzed 1,6-addition reactions, highlighting their efficiency in the rapid synthesis of complex functional molecules.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2021
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
Atropisomeric molecules have found proven applications and have shown promising potential in chemistry and medicine. The design of N-heterocyclic carbene (NHC) catalyzed reactions to construct atropisomerically enriched molecules has emerged as an important research topic in recent years. These reactions include kinetic resolutions, asymmetric desymmetrizations, central-to-axial chirality conversions, and cycloadditions.
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May 2020
Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University Kakuma-machi Kanazawa 920-1192 Japan
In nature, a number of enzymes use thiamine diphosphate as a coenzyme to catalyze the pyruvate decarboxylation. The resultant enamine, a so-called "Breslow intermediate," is known to perform single electron transfer to various electron acceptors. Inspired by this enzymatic catalysis, N-heterocyclic carbene (NHC)-catalyzed radical reactions have been developed.
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