Molecular-iodine-catalyzed aerobic oxidative synthesis of β-hydroxy sulfones from alkenes

Kariya, Atsumasa; Yamaguchi, T.; Nobuta, Tomoya; Tada, Norio; Miura, Tsuyoshi; Itoh, Akichika

doi:10.1039/c3ra47863g

Cited by 69 publications

(24 citation statements)

References 26 publications

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“…These aliphatic olefins were expected to create unstable radicals after reaction with sulfonyl radicals. Also, no reaction in the absence of sulfonyl hydrazide (Figure d) indicated the involvement of the sulfonyl radical during the reaction ,…”

Section: Resultsmentioning

confidence: 99%

Iodine‐Triggered Aerobic Oxysulfonylation of Styrenes

2017

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An iodine-triggered dioxygen activation in oxysulfonylation reactions of unactivated olefins using sulfonyl hydrazides and iodine as catalyst is reported here.I no ne pot,n earq uantitative syntheses of b-hydroxysulfones were achieved at 70 8 8C, within 7h,i na cetonitrile and under aerobic conditions.A plausible mechanism is established by radical trapping and 18 Ol abellinge xperiments for the operation-ally simple,e fficienta nd economically viable transformation. Thed irect activation of aerial oxygen under metal-free and mild conditions is proposed for the oxysulfonylation of olefins.

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Section: Resultsmentioning

confidence: 99%

Iodine‐Triggered Aerobic Oxysulfonylation of Styrenes

2017

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“…The oxidative addition of sodium sulfinates to terminal alkenes can be catalyzed by molecular iodine in the presence of air. 77 Oxygen acts as terminal oxidant, while iodine serves as radical initiator and reducing agent for the initially formed β-hydroperoxo sulfone (Scheme 40).…”

Section: Scheme 39mentioning

confidence: 99%

Recent Advances in the Synthesis of Sulfones

2016

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Sulfones are versatile intermediates in organic synthesis and important building blocks in the construction of biological active molecules or functional materials. This review provides a summary of recent developments in the synthesis of sulfones. 1 Introduction 2 Classical Methods and Variants 2.1 Oxidation of Sulfides 2.2 Aromatic Sulfonylation 2.3 Alkylation/Arylation of Sulfinates 2.4 Addition to Alkenes and Alkynes 2.5 Miscellaneous Methods 3 Metal-Catalyzed Coupling Reactions 4 Sulfone Synthesis by C-H Functionalization 5 Sulfur Dioxide Based Three-Component Approaches 6 Biological Synthesis of Sulfones 7 Conclusion

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“…[64] In contrast to sulfonyl hydrazides, the reaction of sodium sulfinates with styrenes under air proceeded successfully in the absence of pyridine with only 0.1 eq of iodine. [65] The mechanism of the process, as in the case of transition metals usage, is radical: the key intermediate is sulfonyl radical A, which is formed by the reaction between sulfonyl hydrazide 110 and iodine under air. After that, radical A is added to styrene 109 to form benzyl radical B, which is then trapped by oxygen.…”

Section: Synthesis Of β-Hydroxysulfonesmentioning

confidence: 99%

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

et al. 2020

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Oxidative coupling methodology is widely applied for the formation of carbon-carbon and carbon-heteroatom bonds. This review focuses on methods for oxidative sulfonylation of multiple bonds involving sulfonyl hydrazides, sulfinic acids and their salts as sulfonylation reagents. Under oxidative conditions, they generate sulfonyl radicals, trapped by multiple carbon-carbon bonds resulting in a variety of SO 2-containing products: mainly, vinyl and alkynyl sulfones, hydroxy-, keto, and halo-substituted sulfones, sulfonylated derivatives of carbo-and heterocycles. This exhaustive review summarizes 321 references from 1996 to 2020 with the specialization of the studies of the last five years, and is divided into the chapters according to the classes of compounds being sulfonylated.

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Molecular-iodine-catalyzed aerobic oxidative synthesis of β-hydroxy sulfones from alkenes

Abstract: The synthesis of β-hydroxy sulfones from alkenes and sodium sulfinates under aerobic oxidative conditions was achieved in the presence of a catalytic amount of molecular iodine.

Cited by 69 publications

References 26 publications

Iodine‐Triggered Aerobic Oxysulfonylation of Styrenes

Iodine‐Triggered Aerobic Oxysulfonylation of Styrenes

Recent Advances in the Synthesis of Sulfones

Oxidative Sulfonylation of Multiple Carbon‐Carbon bonds with Sulfonyl Hydrazides, Sulfinic Acids and their Salts

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