ArticleJournal of the American Chemical Society2019
CuH-Catalyzed Enantioselective Alkylation of Indole Derivatives with Ligand-Controlled Regiodivergence.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Impact-Tolerant Batteries Enabled by High-Conductivity Shear Thickening Electrolytes.Small (Weinheim an der Bergstrasse, Germany) · 2026Article
- Preparation of 1,4-Diamines by Enantio- and Diastereoselective Cu-Josiphos-Catalyzed Reductive Couplings of Azatrienes and Imines: Regiodivergence Enabled by Catalyst Structure and Reagent Tailoring.Journal of the American Chemical Society · 2025Article
- Late-Stage N-Alkenylative Modifications of Indolic Scaffolds with Propiolates: Toward Bisconjugation and Macrocyclization.Organic letters · 2025Article
- Crystal structure of Staudtienic acid, a diterpenoid fromActa crystallographica. Section E, Crystallographic communications · 2024Article
- Enantioselective synthesis of chiral α,α-dialkyl indoles and related azoles by cobalt-catalyzed hydroalkylation and regioselectivity switch.Nature communications · 2024Article
- Base-Catalyzed Nucleophilic Addition Reaction of Indoles with Vinylene Carbonate: An Approach to Synthesize 4-Indolyl-1,3-dioxolanones.Molecules (Basel, Switzerland) · 2023Article
- Regio- and enantioselective CuH-catalyzed 1,2- and 1,4-hydrosilylation of 1,3-enynes.Nature communications · 2023Article
- Azolation of Benzylic C-H Bonds via Photoredox-Catalyzed Carbocation Generation.Journal of the American Chemical Society · 2023Article
- Copper-Catalyzed Highly Enantioselective Addition of a Silicon Nucleophile to 3-Substituted 2H-Azirines Using an Si-B Reagent.Angewandte Chemie (International ed. in English) · 2023Article
- Enantioselective synthesis of N-alkylindoles enabled by nickel-catalyzed C-C coupling.Nature communications · 2022Article
- Enantioselective Synthesis ofJournal of the American Chemical Society · 2022Article
- Palladium-Catalyzed Oxidative Amination of α-Olefins with Indoles.Organic letters · 2022Article
- Article
- Access to Metal Centers and Fluxional Hydride Coordination Integral for COInorganic chemistry · 2021Article
- Enantioselective C2-Allylation of Benzimidazoles Using 1,3-Diene Pronucleophiles.Organic letters · 2021Article
- Selectivity in the Addition of Electron Deficient Radicals to theEuropean journal of organic chemistry · 2020Article
- CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.Accounts of chemical research · 2020Article
- Highly Enantioselective Synthesis of Indazoles with a C3-Quaternary Chiral Center Using CuH Catalysis.Journal of the American Chemical Society · 2020Article
- Synthesis of Pyrroles through the CuH-Catalyzed Coupling of Enynes and Nitriles.Journal of the American Chemical Society · 2020Article
- PAngewandte Chemie (International ed. in English) · 2020Article
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5 authors.
Funding
Abstract
Enantioenriched molecules bearing indole-substituted stereocenters form a class of privileged compounds in biological, medicinal, and organic chemistry. Thus, the development of methods for asymmetric indole alkylation is highly valuable in organic synthesis. Traditionally, achieving N-selectivity in indole alkylation reactions is a significant challenge, since there is an intrinsic preference for alkylation at C3, the most nucleophilic position. Furthermore, selective and predictable access to either N- or C3-alkylated chiral indoles using catalyst control has been a long-standing goal in indole functionalization. Herein, we report a ligand-controlled regiodivergent synthesis of N- and C3-alkylated chiral indoles that relies on a polarity reversal strategy. In contrast to conventional alkylation reactions in which indoles are employed as nucleophiles, this transformation employs electrophilic indole derivatives, N-(benzoyloxy)indoles, as coupling partners. N- or C3-alkylated indoles are prepared with high levels of regio- and enantioselectivity using a copper hydride catalyst. The regioselectivity is governed by the use of either DTBM-SEGPHOS or Ph-BPE as the supporting ligand. Density functional theory (DFT) calculations are conducted to elucidate the origin of the ligand-controlled regiodivergence.
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