Facile One-Pot Synthesis of Aromatic and Heteroaromatic Sulfonamides

Pandya, Rina; Mutoh, T.; Tedeschi, and Livio; Barrett, Anthony G. M.

doi:10.1021/jo034643j

Cited by 128 publications

(74 citation statements)

References 13 publications

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“…[59][60][61][62] This reaction is particularly attractive as these salts are versatile starting materials for a wide range of sulfonyl-containing functional groups, such as sulfonyl chlorides, [62] sulfonamides, [59] and sulfones. [60,63,64] However, the commercial availability of metal sulfinates is limited to a handful of sodium salts and so the ability to generate them from readily available and easily accessible organometallic reagents expands the scope of the method greatly.…”

Section: Dabso and Organometallic Reagentsmentioning

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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Section: Dabso and Organometallic Reagentsmentioning

confidence: 99%

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

2015

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“…Treatment of the ammonium sulfinate with sulfuryl chloride resulted in oxidative chlorination and allowed isolation of the derived sulfonyl chloride (8). [26] The moderate yield achieved for this transformation reflects isolation issues. The derived sulfonyl chloride intermediates can be combined directly with an amine to deliver sulfonamides.…”

Section: Angewandte Chemiementioning

confidence: 99%

“…The derived sulfonyl chloride intermediates can be combined directly with an amine to deliver sulfonamides. [26] For example, the morpholine derivative 9 was isolated in good yield. Finally, reduction using a Sn/HCl mixture allowed isolation of the corresponding disulfide (10).…”

Section: Angewandte Chemiementioning

confidence: 99%

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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“…8 Treatment of sulfinate 2 with S 8 followed by benzylation afforded S-benzyl alkylthiosulfonates 6. 9,10 (B) Recently, Vogel and co-workers 11 reported a convenient and practical method for the synthesis of sulfinic Lewis acid complex 8 that can be further converted into a range of sulfinyl or sulfonyl derivatives. Chlorination of 8 with NCS yields sulfonyl chloride 9 that can be easily transformed into sulfonamides and sulfonic esters.…”

Section: Introductionmentioning

confidence: 99%

Sulfur Dioxide in the Past Decade

Lugiņina¹

2014

Synlett

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This feature focuses on a reagent chosen by a postgraduate, highlighting the uses and preparation of the reagent in current research 2962 spotlight Sulfur Dioxide in the Past Decade Compiled by Jevgeņija Lugiņina Jevgeņija Lugiņina was born in 1988 in Daugavpils, Latvia. She studied chemistry at Riga Technical University (RTU) where she obtained her Master degree in chemical engineering in 2013. She is currently working towards her Ph.D. under supervision of Professor Maris Turks at RTU. Her research focuses on reactions of organic compounds in liquid sulfur dioxide.

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Facile One-Pot Synthesis of Aromatic and Heteroaromatic Sulfonamides

Cited by 128 publications

References 13 publications

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

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

Sulfur Dioxide in the Past Decade

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