ArticleJournal of the American Chemical Society2017
NHC Ligands Tailored for Simultaneous Regio- and Enantiocontrol in Nickel-Catalyzed Reductive Couplings.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Highly Stereoselective Addition of β-Borylenamides to Aldehydes Enabled by Late‑Stage Ligand Modification.Angewandte Chemie (International ed. in English) · 2026Article
- Article
- Cobalt-catalyzed reductive cross-coupling: a review.Molecular diversity · 2025Review
- Enantioselective electroreductive alkyne-aldehyde coupling.Nature communications · 2025Article
- Heteroaryl-Directed Iridium-Catalyzed Enantioselective C-H Alkenylations of Secondary Alcohols.Journal of the American Chemical Society · 2025Article
- Trialkoxysilane-Induced Iridium-Catalyzed para-Selective C-H Bond Borylation of Arenes.Nature communications · 2024Article
- Enantioselective Metal-Catalyzed Reductive Coupling of Alkynes with Carbonyl Compounds and Imines: Convergent Construction of Allylic Alcohols and Amines.ACS catalysis · 2022Article
- Synthesis of oxaboranesChemical science · 2022Article
- Stereo- and Site-Selective Conversion of Primary Alcohols to Allylic Alcohols via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by 2-Butyne.Journal of the American Chemical Society · 2022Article
- Cross-Selective Aza-Pinacol Coupling via Atom Transfer Catalysis.Journal of the American Chemical Society · 2021Article
- Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA.Molecules (Basel, Switzerland) · 2020Article
- Towards the online computer-aided design of catalytic pockets.Nature chemistry · 2019Review
- Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes.Journal of the American Chemical Society · 2018Article
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6 authors.
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Abstract
An exceptionally hindered class of enantiopure NHC ligands has been developed. While racemic forms had previously been utilized, a scalable and practical route to the enantiopure form of this ligand class is described utilizing a Buchwald-Hartwig N,N-diarylation in a highly sterically demanding environment. Using this newly accessible ligand class, nickel-catalyzed enantioselective reductive coupling reactions of aldehydes and alkynes have been developed. These studies illustrate that the newly available NHC ligands are well suited for simultaneous control of regio- and enantioselectivity, even in cases with internal alkynes possessing only very subtle steric differences between two aliphatic substituents. The steric demand of the new ligand class enables a complementary regiochemical outcome compared with previously described enantioselective processes. Using this method, a number of allylic alcohol derivatives were efficiently obtained with high regioselectivity (up to >95:5) and high enantioselectivity (up to 94% ee). The reaction conditions can also be extended to the reaction of aldehydes and allenes, providing silyl-protected allylic alcohol derivatives possessing a terminal methylene substituent. Computational studies have explained the origin of the exceptional steric demand of this ligand class, the basis for enantioselectivity, and the cooperative relationship of the aldehyde, alkyne, and ligand in influencing enantioselectivity.
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