Iodine-induced synthesis of sulfonate esters from sodium sulfinates and phenols under mild conditions

Pan, Xiaojun; Liu, Juan; Lai, Junyi; Chang, Liming; Yuan, Gaoqing

doi:10.1039/c5ra00724k

Cited by 39 publications

(27 citation statements)

References 72 publications

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“…[11,12] Benziodoxolone-derived iodine(III) compounds are characterized by the presence of an endocyclic iodine, which confers stability, while inverting the polarity of an attached moiety, proving conditions for an umpolung reaction. In addition, similar works have been reported for the formation of sulfonates [15] and sulfones. [12][13][14] Herein, we describe a novel fundamental oxidative process for preparing sulfonamides.…”

Section: Communicationsupporting

confidence: 79%

“…[3] Other methods include metal-catalysed reactions of unsubstituted or mono-substituted sulfonamides, [4] oxidation of sulfonamides or sulfinimides, [5] oxidative coupling reactions between sulfinate salts and amines (Scheme 2B). In addition, similar works have been reported for the formation of sulfonates [15] and sulfones. Recently, DABSO (a complex of 1,4-diazabicyclo[2.2.2]octane with two molecules of SO 2 ) has been widely explored on sulfonylation reactions as an SO 2 surrogate (Scheme 2C).…”

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confidence: 79%

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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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Section: Communicationsupporting

confidence: 79%

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confidence: 79%

Hypervalent Iodine Mediated Sulfonamide Synthesis

et al. 2019

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“…460 Halogenation using molecular iodine has similarly been used for the formation of sulfonic esters via the sulfonyl iodide. 491…”

Section: Sulfinate Salts and Derivativesmentioning

confidence: 99%

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

et al. 2019

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Organosulfur compounds have long played a vital role in organic chemistry and in the development of novel chemical structures and architectures. Prominent among these organosulfur compounds are those involving a sulfur(IV) center, which have been the subject of countless investigations over more than a hundred years. In addition to a long list of textbook sulfur-based reactions, there has been a sustained interest in the chemistry of organosulfur(IV) compounds in recent years. Of particular interest within organosulfur chemistry is the ease with which the synthetic chemist can effect a wide range of transformations through either bond formation or bond cleavage at sulfur. This review aims to cover the developments of the past decade in the chemistry of organic sulfur(IV) molecules and provide insight into both the wide range of reactions which critically rely on this versatile element and the diverse scaffolds that can thereby be synthesized.

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“…Oxidative sulfonate production methods employing strong oxidizing agents such as chlorine have been previously reported [ 30 ]. More recently, a mild and efficient method enabling the production of aromatic sulfonates using phenols and iodine was developed [ 31 – 32 ]. This method uses methanol as a solvent and appears to be selective for phenols; only two primary alcohol examples were produced in 63–67% yield in the presence of a strong base.…”

Section: Resultsmentioning

confidence: 99%

Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent

Deruer¹,

Hamel²,

Blais³

et al. 2018

Beilstein J. Org. Chem.

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An alternative method for forming sulfonates through hypervalent iodine(III) reagent-mediated oxidation of sodium sulfinates has been developed. This transformation involves trapping reactive sulfonium species using alcohols. With additional optimization of the reaction conditions, the method appears extendable to other nucleophiles such as electron-rich aromatic systems or cyclic ethers through a ring opening pathway.

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Iodine-induced synthesis of sulfonate esters from sodium sulfinates and phenols under mild conditions

Abstract: A facile and highly efficient method for the synthesis of sulfonate esters mediated by iodine at room temperature has been developed, without transition metal catalysts and oxidants.

Cited by 39 publications

References 72 publications

Hypervalent Iodine Mediated Sulfonamide Synthesis

Hypervalent Iodine Mediated Sulfonamide Synthesis

Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts

Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent

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