Copper-catalyzed sulfonamides formation from sodium sulfinates and amines

Tang, Xiaodong; Huang, Liangbin; Qi, Chaorong; Wu, Xia; Wu, Wanqing; Jiang, Huanfeng

doi:10.1039/c3cc41249k

Cited by 157 publications

(79 citation statements)

References 56 publications

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“…However, when benzo [1,2,3]triazole was allowed to react with 2a under the standard conditions, the expected product 3p was not generated; instead, 1-methoxybenzo [1,2,3]triazole was isolated in an 8% yield.…”

Section: Scheme 2 Electrochemically Oxidative Amination Of Sodium Bementioning

confidence: 88%

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH₄I as a Redox Catalyst

et al. 2016

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An efficient protocol for the synthesis of sulfonamides via the electrochemical oxidative amination of sodium sulfinates has been developed. The chemistry proceeds in a simple undivided cell employing a substoichiometric amount of NH4I that serves both as a redox catalyst and a supporting electrolyte; in this manner additional conducting salt is not required. A wide range of substrates, including aliphatic or aromatic secondary and primary amines, as well as aqueous ammonia, proved to be compatible with the protocol. Scale-up was possible, thereby demonstrating the practicality of the approach. The electrolytic process avoids the utilization of external oxidants or corrosive molecular iodine and therefore represents an environmentally benign means by which to achieve the transformation.

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Section: Scheme 2 Electrochemically Oxidative Amination Of Sodium Bementioning

confidence: 88%

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH₄I as a Redox Catalyst

et al. 2016

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“…As an alternative, a new and convenient method for the construction of sulfonamides via a copper-catalyzed oxidative coupling between sodium sulfinates and amines with O 2 (1 atm) or DMSO as the oxidant was described by Jiang et al [12] (Fig. 5).…”

Section: Synthesis Of Sulfonamidesmentioning

confidence: 99%

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Feng¹,

Tang²,

Liang³

et al. 2016

CTMC

1,512

641

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The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and natural products. For centuries, sulfur continues to maintain its status as the dominating heteroatom integrated into a set of 362 sulfur-containing FDA approved drugs (besides oxygen or nitrogen) through the present. Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades. In this review, these four moieties in pharmaceuticals and recent advances in the synthesis of the corresponding core scaffolds are presented.

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“…

A new metal-free sulfonylation reaction is described. [6][7][8] These methods either use harsh conditions, non-environmentally friendly reagents or are limited in scope. 2695 clean and mild transfer of sulfonyl groups to amines and anilines.

…”

mentioning

confidence: 99%

Hypervalent Iodine Mediated Sulfonamide Synthesis

et al. 2019

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A new metal‐free sulfonylation reaction is described. The method takes advantage of the Umpolung reactivity and group‐transfer properties of iodine(III) compounds, combining hypervalent iodine reagents and sulfinate salts to deliver a clean and mild transfer of sulfonyl groups to amines and anilines. A total of 25 sulfonamides was synthesised in up to 99 % yield, even on gram‐scale. The reaction mechanism was investigated by ESI‐MS and DFT calculations.

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Copper-catalyzed sulfonamides formation from sodium sulfinates and amines

Cited by 157 publications

References 56 publications

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH₄I as a Redox Catalyst

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH₄I as a Redox Catalyst

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Hypervalent Iodine Mediated Sulfonamide Synthesis

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Copper-catalyzed sulfonamides formation from sodium sulfinates and amines

Cited by 157 publications

References 56 publications

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH4I as a Redox Catalyst

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH4I as a Redox Catalyst

Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry

Hypervalent Iodine Mediated Sulfonamide Synthesis

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Product

Resources

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Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH₄I as a Redox Catalyst

Electrochemical Oxidative Amination of Sodium Sulfinates: Synthesis of Sulfonamides Mediated by NH₄I as a Redox Catalyst