ArticleNature communications2021
Autocatalytic photoredox Chan-Lam coupling of free diaryl sulfoximines with arylboronic acids.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 68 citations in OpenAlex.
- Rhodium-CatalyzedACS omega · 2026Article
- Shedding Light on Synthetic Autocatalysis: From Conventional Closed-Shell Chemistries to Overlooked Open-Shell Occurrences.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Mild N‑Arylation of Sulfoximines With (Hetero)aryl Chlorides Enabled by α-Methylnaphthyl-tBuBrettPhos Palladium Triflate.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- π-Electron Donation at the Sulfoximidoyl Nitrogen Atom.Angewandte Chemie (International ed. in English) · 2025Article
- Electrochemically promoted defluorinative sulfoximination and fluorosulfonylation of non-activated aryl fluorides at room temperature.Chemical science · 2025Article
- Photoinduced Autopromoted Ni-Catalyzed Three-Component Arylsulfonation Inspired by Density Functional Theory/Time-Dependent Density Functional Theory-Simulated Photoactive Nickel Species.Organic letters · 2025Article
- Synthesis of Sulfilimines Enabled by Copper-CatalyzedJournal of the American Chemical Society · 2023Article
- Ligand-to-Copper Charge-Transfer-Enabled C-H Sulfoximination of Arenes.Organic letters · 2023Article
- Catalytically active atomically thin cuprate with periodic Cu single sites.National science review · 2023Article
- Direct formation and site-selective elaboration of methionine sulfoximine in polypeptides.Chemical science · 2022Article
- Decarboxylative sulfoximination of benzoic acids enabled by photoinduced ligand-to-copper charge transfer.Chemical science · 2022Article
- Biomolecule-Compatible Dehydrogenative Chan-Lam Coupling of Free Sulfilimines.Journal of the American Chemical Society · 2022Article
Corrections and comments
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Authors and funding
9 authors at 4 institutions in 2 countries.
Funding
Abstract
N-Arylation of NH-sulfoximines represents an appealing approach to access N-aryl sulfoximines, but has not been successfully applied to NH-diaryl sulfoximines. Herein, a copper-catalyzed photoredox dehydrogenative Chan-Lam coupling of free diaryl sulfoximines and arylboronic acids is described. This neutral and ligand-free coupling is initiated by ambient light-induced copper-catalyzed single-electron reduction of NH-sulfoximines. This electron transfer route circumvents the sacrificial oxidant employed in traditional Chan-Lam coupling reactions, increasing the environmental friendliness of this process. Instead, dihydrogen gas forms as a byproduct of this reaction. Mechanistic investigations also reveal a unique autocatalysis process. The C-N coupling products, N-arylated sulfoximines, serve as ligands along with NH-sulfoximine to bind to the copper species, generating the photocatalyst. DFT calculations reveal that both the NH-sulfoximine substrate and the N-aryl product can ligate the copper accounting for the observed autocatalysis. Two energetically viable stepwise pathways were located wherein the copper facilitates hydrogen atom abstraction from the NH-sulfoximine and the ethanol solvent to produce dihydrogen. The protocol described herein represents an appealing alternative strategy to the classic oxidative Chan-Lam reaction, allowing greater substrate generality as well as the elimination of byproduct formation from oxidants.
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