ReviewAngewandte Chemie (International ed. in English)2020
Sulfonate N-Heterocyclic Carbene-Copper Complexes: Uniquely Effective Catalysts for Enantioselective Synthesis of C-C, C-B, C-H, and C-Si Bonds.
Review in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Enantioselective Synthesis of a New Class of Stable and Functionalized Cyclopentadienes via CuH-Catalysis.Angewandte Chemie (International ed. in English) · 2026Article
- Divergent and programmable skeletal remodeling of complex macrocycles with a small method set.Science (New York, N.Y.) · 2026Article
- Design Approaches That Utilize Ionic Interactions to Control Selectivity in Transition Metal Catalysis.Chemical reviews · 2025Review
- Recent advances in allylation of chiral secondary alkylcopper species.Beilstein journal of organic chemistry · 2025Review
- Catalytic prenyl conjugate additions for synthesis of enantiomerically enriched PPAPs.Science (New York, N.Y.) · 2024Article
- Copper-catalyzed asymmetric allylic substitution of racemic/Chemical science · 2024Review
- Copper-catalyzed yne-allylic substitutions: concept and recent developments.Beilstein journal of organic chemistry · 2024Review
- Structurally divergent enantioselective synthesis of benzofuran fused azocine derivatives and spiro-cyclopentanone benzofurans enabled by sequential catalysis.Chemical science · 2023Article
- Catalytic Alkyne Allylboration: A Quest for Selectivity.ACS catalysis · 2023Review
- Axially chiral styrene-based organocatalysts and their application in asymmetric cascade Michael/cyclization reaction.Chemical science · 2023Article
- Copper-Catalyzed Enantioselective Borylative Allyl-Allyl Coupling of Allenes and AllylicACS catalysis · 2023Article
- Catalytic Cross-Metathesis Reactions That AffordJournal of the American Chemical Society · 2023Article
- Copper-Catalyzed Coupling of Alkyl Vicinal Bis(boronic Esters) to an Array of Electrophiles.Journal of the American Chemical Society · 2022Article
- Enantio- and Diastereoselective Copper-Catalyzed Allylboration of Alkynes with Allylic gem-Dichlorides.Angewandte Chemie (International ed. in English) · 2022Article
- Solvent directed chemically divergent synthesis of β-lactams and α-amino acid derivatives with chiral isothiourea.Chemical science · 2022Article
- Zinc Iodide Catalyzed Synthesis of Trisubstituted Allenes from Terminal Alkynes and Ketones.ACS omega · 2021Article
- Palladium-catalyzed asymmetric allylic alkylation (AAA) with alkyl sulfones as nucleophiles.Chemical science · 2021Article
- 1,3-Bis(tricyanoborane)imidazoline-2-ylidenate Anion-A Ditopic Dianionic N-Heterocyclic Carbene Ligand.Angewandte Chemie (International ed. in English) · 2021Article
- BIAN-NHC Ligands in Transition-Metal-Catalysis: A Perfect Union of Sterically Encumbered, Electronically Tunable N-Heterocyclic Carbenes?Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Review
- Beyond Carbon: Enantioselective and Enantiospecific Reactions with Catalytically Generated Boryl- and Silylcopper Intermediates.ACS central science · 2020Review
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Authors and funding
6 authors.
Funding
Abstract
A copper-based complex that contains a sulfonate N-heterocyclic carbene ligand was first reported 15 years ago. Since then, these organometallic entities have proven to be uniquely effective in catalyzing an assortment of enantioselective transformations, including allylic substitutions, conjugate additions, proto-boryl additions to alkenes, boryl and silyl substitutions, hydride-allyl additions to alkenyl boronates, and additions of boron-containing allyl moieties to N-H ketimines. In this review article, we detail the shortcomings in the state-of-the-art that fueled the development of this air stable ligand class, members of which can be prepared on multigram scale. For each reaction type, when relevant, the prior art at the time of the advance involving sulfonate NHC-Cu catalysts and/or subsequent key developments are briefly analyzed, and the relevance of the advance to efficient and enantioselective total or formal synthesis of biologically active molecules is underscored. Mechanistic analysis of the structural attributes of sulfonate NHC-Cu catalysts that are responsible for their ability to facilitate transformations with high efficiency as well as regio- and enantioselectivity are detailed. This review contains several formerly undisclosed methodological advances and mechanistic analyses, the latter of which constitute a revision of previously reported proposals.
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