Photoredox-Catalyzed Hydrosulfonylation of Arylallenes

Storozhenko, Olga А.; Festa, Alexey А.; Detistova, Galina I; Rybakov, Victor B.; Варламов, А. В.; Eycken, Erik V. Van der; Voskressensky, Leonid G.

doi:10.1021/acs.joc.9b02960

Cited by 32 publications

(24 citation statements)

References 74 publications

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“…The SET oxidation of sulfinic acids and sulfinates for the generation of sulfonyl radicals has been thoroughly explored over the past decades [172]. These oxidations occur under mildly oxidative conditions, and eosin Y (OD13) stands out as an efficient photocatalyst for these steps [175][176][177]. This strategy is also compatible with transition metal catalysis, as shown by Lei and co-workers with an organophotocatalyzed radical cross-coupling method using the aryl sulfinic acids 45.1 and the styrenes 45.2 to generate the allyl sulfones 45.3 (Scheme 45) [178].…”

Section: Scheme 44mentioning

confidence: 99%

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Amos¹,

Garreau²,

Buzzetti³

et al. 2020

Beilstein J. Org. Chem.

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Organic dyes have emerged as a reliable class of photoredox catalysts. Their great structural variety combined with the easy fine-tuning of their electronic properties has unlocked new possibilities for the generation of reactive intermediates. In this review, we provide an overview of the available approaches to access reactive intermediates that employ organophotocatalysis. Our contribution is not a comprehensive description of the work in the area but rather focuses on key concepts, accompanied by a few selected illustrative examples. The review is organized along the type of reactive intermediates formed in the reaction, including C(sp3) and C(sp 2 ) carbon-, nitrogen-, oxygen-, and sulfur-centered radicals, open-shell charged species, and sensitized organic compounds.

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Section: Scheme 44mentioning

confidence: 99%

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Amos¹,

Garreau²,

Buzzetti³

et al. 2020

Beilstein J. Org. Chem.

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“…[27] When arylallenes were used as starting compounds in photo- catalytic sulfonylation with sodium sulfinates, the regio-and diastereoselective formation of vinyl sulfones was observed. [28] A photocatalytic approach was also used to synthesize allyl sulfones 37 from styrenes 35 and aryl, hetaryl, and alkyl sulfinic acids 36. [29] The reaction proceeded in chloroform in the presence of (Bu 4 N) 2eosin Y as the photocatalyst as well as Co(dmgH) 2 pyCl and pyridine.…”

Section: Sulfonylation Of Alkenesmentioning

confidence: 99%

“…Photocatalytic sulfonylation of alkenes with sodium sulfinates in the presence of the iridium‐based photocatalyst in DCM led to the formation of hydrosulfonylation products in 13–99% yields [27] . When arylallenes were used as starting compounds in photocatalytic sulfonylation with sodium sulfinates, the regio‐ and diastereoselective formation of vinyl sulfones was observed [28] …”

Section: Sulfonylation Of Unactivated Multiple Bondsmentioning

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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“…In 2020, Voskressensky group found that arylallenes were suitable substrates for photoredox-catalyzed hydrosulfonylation with sodium sulfinates. [22] Sulfonyl radical which was derived from the quenching reaction of the excited photocatalyst eosin Y* with sodium sulfinates was proposed. While the aliphatic allenes were not suitable for this method (Scheme 14).…”

Section: Sulfonylation/noncyclization With Alkenesmentioning

confidence: 99%

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

et al. 2020

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Sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides as readily available and efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these sulfonyl reagents via different methods, then the sulfonyl radical could react with various substrates via different pathways to afford the corresponding products. In this review, we will summarize the progress in sulfonylation via radical reaction using sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides in recent three years. In terms of the different sulfonylation reagents, we classify these sulfonylation reactions into four types: 1.

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Photoredox-Catalyzed Hydrosulfonylation of Arylallenes

Cited by 32 publications

References 74 publications

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

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

Recent Progress in Sulfonylation via Radical Reaction with Sodium Sulfinates, Sulfinic Acids, Sulfonyl Chlorides or Sulfonyl Hydrazides

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