ArticleAngewandte Chemie (International ed. in English)2019
Organophosphorus-Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by P
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Article
- Peptide-Catalyzed Asymmetric Amination of Sulfenamides Enabled by DFT-Guided Catalyst Optimization.Journal of the American Chemical Society · 2025Article
- Beyond BODIPY: dipyrrin complexes of P-block elements.Journal of coordination chemistry · 2025Article
- Iodophor-catalyzed sulfenylation of indoles with sulfonyl hydrazides for the synthesis of 3-sulfenylindoles.RSC advances · 2024Article
- Cobalt- or rhodium-catalyzed synthesis of 1,2-dihydrophosphete oxidesChemical science · 2024Article
- Expanding Reaction Profile of Allyl Carboxylates via 1,2-Radical Migration (RaM): Visible-Light-Induced Phosphine-Catalyzed 1,3-Carbobromination of Allyl Carboxylates.Journal of the American Chemical Society · 2023Article
- Efficient Synthesis of 3-Mercaptoindoles via HI-Promoted Sulfenylation of Indoles with Sodium Sulfinates.ChemistryOpen · 2023Article
- Direct fluoroalkylthiolation of indoles with iodofluoroethane enabled by NaRSC advances · 2022Article
- Enantioselective Synthesis of Quaternary Oxindoles: Desymmetrizing Staudinger-Aza-Wittig Reaction Enabled by a Bespoke HypPhos Oxide Catalyst.Journal of the American Chemical Society · 2022Article
- Chemoselective Primary Amination of Aryl Boronic Acids by PJournal of the American Chemical Society · 2022Article
- Phosphorus-Based Catalysis.ACS central science · 2021Review
- Main Group Redox Catalysis of Organopnictogens: Vertical Periodic Trends and Emerging Opportunities in Group 15.Journal of the American Chemical Society · 2021Article
- Organophosphorus-catalyzed relay oxidation of H-Bpin: electrophilic C-H borylation of heteroarenes.Chemical science · 2020Article
- Catalytic Activation of NJournal of the American Chemical Society · 2020Article
- P(III)/P(V)-Catalyzed Methylamination of Arylboronic Acids and Esters: Reductive C-N Coupling with Nitromethane as a Methylamine Surrogate.Journal of the American Chemical Society · 2020Article
- Let's Make White Phosphorus Obsolete.ACS central science · 2020Review
- An Improved PJournal of the American Chemical Society · 2020Article
- Article
- PAngewandte Chemie (International ed. in English) · 2020Article
- Reduction of Activated Alkenes by PAngewandte Chemie (International ed. in English) · 2020Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
A method for electrophilic sulfenylation by organophosphorus-catalyzed deoxygenative O-atom transfer from sulfonyl chlorides is reported. This C-S bond-forming reaction is catalyzed by a readily available small-ring phosphine (phosphetane) in conjunction with a hydrosilane terminal reductant to afford a general entry to sulfenyl electrophiles, including valuable trifluoromethyl, perfluoroalkyl, and heteroaryl derivatives that are otherwise difficult to access. Mechanistic investigations indicate that the twofold deoxygenation of the sulfonyl substrate proceeds by the intervention of an off-cycle resting state thiophosphonium ion. The catalytic method represents an operationally simple protocol using a stable phosphine oxide as a precatalyst and exhibits broad functional-group tolerance.
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