ArticleChemical science2022
Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation.
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 102 citations in OpenAlex.
- Highly chemoselective access to alkyl-sulfur compounds via NNature chemistry · 2026Article
- Direct photochemical activation of aliphatic carboxylic acids toward phosphinylationChemical science · 2026Article
- Acridine/Lewis acid photocatalysis enables α-amidyl radical cyclizations.Organic chemistry frontiers : an international journal of organic chemistry · 2026Article
- Article
- Acridinium amidate as a hydrogen-bonding photocatalyst for direct decarboxylative alkylation of native carboxylic acids.Chemical science · 2026Article
- Photocatalytic multicomponent alkene dicarbofunctionalizationChemical science · 2026Article
- Photoredox-Neutral Platform for Direct Decarboxylative CyclopropanationACS catalysis · 2026Article
- Dispersion-Enhanced Nitrogen-Centered Photocatalysis of the Direct Hydrogen Atom Transfer.Angewandte Chemie (International ed. in English) · 2026Article
- Photoredox-controlled chemo-divergent, regio-, and stereoselective difunctionalization of olefins via switchable SOScience advances · 2025Article
- Carbon-Heteroatom Bond Formation via Photoinduced Decarboxylative Radical Coupling Reactions.ACS omega · 2025Review
- N-Protonated Acridinium Catalyst Enables Anti-Markovnikov Hydration of Unconjugated Tri- and Disubstituted Olefins.Journal of the American Chemical Society · 2025Article
- Acridine/Lewis Acid Complexes as Powerful Photocatalysts: A Combined Experimental and Mechanistic Study.ACS catalysis · 2024Article
- Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BFJournal of the American Chemical Society · 2024Article
- Acridine photocatalysis enables tricomponent direct decarboxylative amine construction.Chemical science · 2024Article
- Multimodal Acridine Photocatalysis Enables Direct Access to Thiols from Carboxylic Acids and Elemental Sulfur.ACS catalysis · 2024Article
- Direct conversion of carboxylic acids to free thiolsChemical science · 2024Article
- Alkanes in Minisci-Type Reaction under Photocatalytic Conditions with Hydrogen Evolution.Organic letters · 2023Article
- Kinetically-driven reactivity of sulfinylamines enables direct conversion of carboxylic acids to sulfinamides.Chemical science · 2023Article
- One-Pot Synthesis of Sulfonamides from Unactivated Acids and Amines via Aromatic Decarboxylative Halosulfonylation.Journal of the American Chemical Society · 2023Article
- Photoredox Catalysis-Enabled Sulfination of Alcohols and Bromides.Journal of the American Chemical Society · 2023Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
The reactivity of the sulfonyl group varies dramatically from nucleophilic sulfinates through chemically robust sulfones to electrophilic sulfonyl halides-a feature that has been used extensively in medicinal chemistry, synthesis, and materials science, especially as bioisosteric replacements and structural analogs of carboxylic acids and other carbonyls. Despite the great synthetic potential of the carboxylic to sulfonyl functional group interconversions, a method that can convert carboxylic acids directly to sulfones, sulfinates and sulfonyl halides has remained out of reach. We report herein the development of a photocatalytic system that for the first time enables direct decarboxylative conversion of carboxylic acids to sulfones and sulfinates, as well as sulfonyl chlorides and fluorides in one step and in a multicomponent fashion. A mechanistic study prompted by the development of the new method revealed the key structural features of the acridine photocatalysts that facilitate the decarboxylative transformations and provided an informative and predictive multivariate linear regression model that quantitatively relates the structural features with the photocatalytic activity.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.