Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides

Shavnya, Andrei; Coffey, Steven B.; Smith, Aaron; Mascitti, Vincent

doi:10.1021/ol403072r

Cited by 216 publications

(77 citation statements)

References 13 publications

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“…to give the corresponding sulfonamide 20 (63%). Reaction of this substrate with morpholine under the conditions described by Shavnya et al 15 gave the corresponding sulfonamide 21 in 77% yield. Unfortunately, complex mixtures of products were observed when performing this protocol using aniline or primary amine starting materials.…”

mentioning

confidence: 89%

“…Sulfonamide 26 was reacted with morpholine under the conditions described by Shavnya et al, 15 however, a complex mixture of products was observed by LCMS. A modest yield (48%) of 21 was achieved by using 5 equivalents of K2S2O5, however, despite extensive exploration of reaction conditions, a number of unidentified products predominated when using primary amines or anilines in this reaction.…”

Section: Scheme 3 Preparation Of Iodo Sulfonamidesmentioning

confidence: 99%

“…15 With this in mind, we envisaged non-symmetrical bis-sulfonamides could be accessed by the route outlined in Scheme 1.…”

mentioning

confidence: 99%

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Preparation of Symmetrical and Nonsymmetrical Fluorene Sulfonamide Scaffolds

Jones

Tellam

Bresciani

et al. 2016

Synlett

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This version is available at https://strathprints.strath.ac.uk/61052/ Strathprints is designed to allow users to access the research output of the University of Strathclyde. Unless otherwise explicitly stated on the manuscript, Copyright © and Moral Rights for the papers on this site are retained by the individual authors and/or other copyright owners. Please check the manuscript for details of any other licences that may have been applied. You may not engage in further distribution of the material for any profitmaking activities or any commercial gain. You may freely distribute both the url (https://strathprints.strath.ac.uk/) and the content of this paper for research or private study, educational, or not-for-profit purposes without prior permission or charge.Any correspondence concerning this service should be sent to the Strathprints administrator: strathprints@strath.ac.ukThe Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. P -Abstract Methods for the preparation of symmetrical and non-symmetrical 2,7-disubstituted 9H-fluorene derivatives are described.

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confidence: 89%

Section: Scheme 3 Preparation Of Iodo Sulfonamidesmentioning

confidence: 99%

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Preparation of Symmetrical and Nonsymmetrical Fluorene Sulfonamide Scaffolds

Jones

Tellam

Bresciani

et al. 2016

Synlett

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“…A group from Pfizer utilised the K 2 S 2 O 5 surrogate to develop their sulfination reaction (Scheme 17). [82] Using Pd(OAc) 2 /PPh 3 /1,10-phenanthroline (5/ 15/15 mol %) catalytic conditions, they required sodium formate and TBAB as a stoichiometric reductant/additive, respectively, to achieve the desired coupling of SO 2 and (hetero)aryl halides in DMSO or MeCN. They exemplified this reaction with telescoped reactions of the sulfinate to form sulfones via alkylation, and in addition, sulfonamides through bromination and subsequent amination of the sulfonyl bromide.…”

Section: New Chemistry Of So 2 : Palladium-catalysed Sulfonylationsmentioning

confidence: 99%

The Development and Application of Sulfur Dioxide Surrogates in Synthetic Organic Chemistry

2015

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Sulfur dioxide has a rich and varied chemistry that can be traced back to the early 1900s. Despite the potential utility of sulfur dioxide based reactions, delivering products such as sulfones, sulfonamides and sulfinic acids, the number of examples of these reactions being exploited in synthesis is arguably lower than would be expected. One significant contributing factor to this is undoubtedly the toxic and gaseous nature of SO2. One strategy to overcome this limitation is to employ an equivalent, or surrogate, so that the gaseous reagent is no longer needed. This strategy has proven to be a success, with a number of methods being described. The reactions reported include variants of traditional reactions in which the gaseous reagent has been replaced with a surrogate, and also new transformations for which no gaseous reaction is known. This Focus Review discusses the origin of sulfur dioxide surrogates and then considers their application to synthetic organic chemistry.

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“…However, the process requires high ligand loadings (30 mol %), the use of an excess of inorganic reductant, as well as a stoichiometric additive (TBAB). [18] Herein we describe an operationally simple protocol which employs only DABSO, triethylamine, and isopropyl alcohol, in combination with a low palladium and ligand loading to convert aryl halides into the corresponding ammonium sulfinates [Eq. (3)].…”

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Palladium‐Catalyzed Synthesis of Ammonium Sulfinates from Aryl Halides and a Sulfur Dioxide Surrogate: A Gas‐ and Reductant‐Free Process

2014

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Sulfonyl-derived functional groups populate a broad range of useful molecules and materials, and despite a variety of preparative methods being available, processes which introduce the most basic sulfonyl building block, sulfur dioxide, using catalytic methods, are rare. Described herein is a simple reaction system consisting of the sulfur dioxide surrogate DABSO, triethylamine, and a palladium(0) catalyst for effective convertion of a broad range of aryl and heteroaryl halides into the corresponding ammonium sulfinates. Key features of this gas-and reductant-free reaction include the low loadings of palladium (1 mol %) and ligand (1.5 mol %) which can be employed, and the use of isopropyl alcohol as both a solvent and formal reductant. The ammonium sulfinate products are converted in situ into a variety of sulfonylcontaining functional groups, including sulfones, sulfonyl chlorides, and sulfonamides.

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Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides

Cited by 216 publications

References 13 publications

Preparation of Symmetrical and Nonsymmetrical Fluorene Sulfonamide Scaffolds

Preparation of Symmetrical and Nonsymmetrical Fluorene Sulfonamide Scaffolds

The Development and Application of Sulfur Dioxide Surrogates in Synthetic Organic Chemistry

Palladium‐Catalyzed Synthesis of Ammonium Sulfinates from Aryl Halides and a Sulfur Dioxide Surrogate: A Gas‐ and Reductant‐Free Process

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Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides

Cited by 216 publications

References 13 publications

Preparation of Symmetrical and Nonsymmetrical Fluorene ­Sulfonamide Scaffolds

Preparation of Symmetrical and Nonsymmetrical Fluorene ­Sulfonamide Scaffolds

The Development and Application of Sulfur Dioxide Surrogates in Synthetic Organic Chemistry

Palladium‐Catalyzed Synthesis of Ammonium Sulfinates from Aryl Halides and a Sulfur Dioxide Surrogate: A Gas‐ and Reductant‐Free Process

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Preparation of Symmetrical and Nonsymmetrical Fluorene Sulfonamide Scaffolds

Preparation of Symmetrical and Nonsymmetrical Fluorene Sulfonamide Scaffolds