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Chemodivergent, enantio- and regioselective couplings of alkynes, aldehydes and silanes enabled by nickel/N-heterocyclic carbene catalysis.
Sci Bull (Beijing)
December 2024
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China. Electronic address:
Divergent synthesis of valuable molecules through common starting materials and metal catalysis represents a longstanding challenge and a significant research goal. We here describe chemodivergent, highly enantio- and regioselective nickel-catalyzed reductive and dehydrogenative coupling reactions of alkynes, aldehydes, and silanes. A single chiral Ni-based catalyst is leveraged to directly prepare three distinct enantioenriched products (silyl-protected trisubstituted chiral allylic alcohols, oxasilacyclopentenes, and silicon-stereogenic oxasilacyclopentenes) in a single chemical operation.
View Article and Find Full Text PDFElectroredox N-Heterocyclic Carbene-Catalyzed Enantioselective (3 + 3) Annulation of Enals with 2-Naphthols.
Org Lett
January 2025
Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar, Punjab 140001, India.
Developing asymmetric transformations using electroredox and N-heterocyclic carbene (NHC)-catalyzed radical pathways is still desirable and challenging. Herein, we report an iodide-promoted β-carbon activation (LUMO-lowering process) of enals via electroredox carbene catalysis coupled with a hydrogen evolution reaction (HER). This strategy offers an environmentally friendly and sustainable route for rapidly assembling synthetically useful chiral naphthopyran-3-one in good to excellent yield and enantioselectivity using traceless electrons as inexpensive and greener oxidants.
View Article and Find Full Text PDFTunable Thiazolium Carbenes for Enantioselective Radical Three-Component Dicarbofunctionalizations.
J Am Chem Soc
December 2024
Laboratory of Asymmetric Catalysis and Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland.
Asymmetric -heterocyclic carbene (NHC) organocatalysis is a cornerstone of synthetic organic chemistry. The emerging concept of single-electron NHC catalysis broadened the scope of C-C bond-forming reactions, facilitating the synthesis of a variety of attractive racemic compounds. However, the development of effective and selective chiral NHC catalysts for asymmetric radical-mediated reactions has been challenging.
View Article and Find Full Text PDFPd/NHC sequentially catalyzed atroposelective synthesis of planar-chiral macrocycles.
Chem Sci
November 2024
School of Pharmaceutical Sciences, Key Laboratory of Bioorganic Phosphorous Chemistry and Chemical Biology, Ministry of Education, Tsinghua University Beijing 100084 China
Planar-chiral macrocycles play a pivotal role in host-guest chemistry and drug discovery. However, compared with the synthesis of other types of chiral compounds, the asymmetric construction of planar-chiral macrocycles still remains a forbidding challenge. Herein, we report a sequential palladium and N-heterocyclic carbene catalysis to build planar-chiral macrocycles.
View Article and Find Full Text PDFSynthesis of Homochiral N-Heterocyclic Carbene-Based Nanosheets for Enhanced Asymmetric Catalysis.
Adv Sci (Weinh)
November 2024
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian, 350002, P. R. China.
Article Synopsis
- * Four pairs of chiral metal-organic layers (MOLs) with N-Heterocyclic carbene (NHC) groups were synthesized, and (S)-1-Zn crystals were successfully delaminated into ultrathin MONs.
- * The resulting (S)-1-Zn nanosheets demonstrated improved yield and enantioselectivity in benzoin condensation reactions, emphasizing their potential in enhancing heterogeneous asymmetric catalysis.
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