ArticleAngewandte Chemie (International ed. in English)2015
Combining organometallic reagents, the sulfur dioxide surrogate DABSO, and amines: a one-pot preparation of sulfonamides, amenable to array synthesis.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Bio-Inspired Photocatalytic Degradation of Humic Acids over TiOBiomimetics (Basel, Switzerland) · 2026Article
- A Sulfoxide Reagent for One-Pot, Three-Component Syntheses of Sulfoxides and Sulfinamides.Angewandte Chemie (International ed. in English) · 2022Article
- An Efficient Method for the Preparation of Sulfonamides from Sodium Sulfinates and Amines.ChemistryOpen · 2022Article
- Visible-light-induced one-pot synthesis of sulfonic estersRSC advances · 2022Article
- Divergent reactivity of sulfinates with pyridinium salts based on one-Chemical science · 2021Article
- Site-Selective C-H Functionalization-Sulfination Sequence to Access Aryl Sulfonamides.Organic letters · 2020Article
- Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents.Angewandte Chemie (International ed. in English) · 2019Article
- Selective Late-Stage Sulfonyl Chloride Formation from Sulfonamides Enabled by Pyry-BFAngewandte Chemie (International ed. in English) · 2019Article
- Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.Chemical reviews · 2019Article
- Efficient synthesis of 3-sulfolenes from allylic alcohols and 1,3-dienes enabled by sodium metabisulfite as a sulfur dioxide equivalent.Organic & biomolecular chemistry · 2018Article
- Double SOACS omega · 2018Article
- Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis.Angewandte Chemie (International ed. in English) · 2018Article
- Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions.Organic letters · 2017Article
- Copper(i)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling.Chemical science · 2017Article
- One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.Chemical science · 2017Article
- Evaluating New Chemistry to Drive Molecular Discovery: Fit for Purpose?Angewandte Chemie (International ed. in English) · 2016Review
- Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.The Journal of organic chemistry · 2016Article
- Palladium(II)-Catalyzed Synthesis of Sulfinates from Boronic Acids and DABSO: A Redox-Neutral, Phosphine-Free Transformation.Angewandte Chemie (International ed. in English) · 2016Article
- Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.Organic letters · 2015Article
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3 authors.
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Abstract
We describe a method for the synthesis of sulfonamides through the combination of an organometallic reagent, a sulfur dioxide equivalent, and an aqueous solution of an amine under oxidative conditions (bleach). This simple reaction protocol avoids the need to employ sulfonyl chloride substrates, thus removing the limitation imposed by the commercial availability of these reagents. The resultant method allows access to new chemical space, and is also tolerant of the polar functional groups needed to impart favorable physiochemical properties required for medicinal chemistry and agrochemistry. The developed chemistry is employed in the synthesis of a targeted 70 compound array, prepared using automated methods. The array achieved a 93% success rate for compounds prepared. Calculated molecular weights, lipophilicities, and polar surface areas are presented, demonstrating the utility of the method for delivering sulfonamides with drug-like properties.
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