Mn(<scp>iii</scp>)-mediated regioselective synthesis of (E)-vinyl sulfones from sodium sulfinates and nitro-olefins

Nie, Gang; Deng, Xiaocong; Xue, Lixin; Hu, Qinquan; Chen, Yunfeng

doi:10.1039/c6ra17842a

Cited by 39 publications

(13 citation statements)

References 91 publications

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“…When nitro groups were present in the aromatic ring of βnitrostyrene 237, the reaction was unsuccessful. [135] During the process, Mn(III) oxidizes sodium sulfinate 238 into sulfonyl radical A. After that, radical A is added to nitroalkene 237 with the formation of intermediate B.…”

Section: Sulfonylation Of β-Nitroalkenesmentioning

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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Section: Sulfonylation Of β-Nitroalkenesmentioning

confidence: 99%

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

et al. 2020

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“…Although each proposal differs in detail, the main three characteristic steps feature in all proposals. Firstly, carbon- or heteroatom-centered radical 4 is generated in situ by various methods from precursors 6 – 33 [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 , 55 , 56 ]. These include a thermal homolytic cleavage of labile bonds, metal-catalyzed and photochemically initiated processes.…”

Section: Nitrostyrene Cross-coupling—the Background and Mechanismsmentioning

confidence: 99%

“…Within three years, between 2016 and 2018, several groups published closely related transformations of nitrostyrenes 1 and sodium salt of aryl sulfinic acids 23 , to form conjugated sulfones 3 ( Scheme 19 ). In 2016, Chen reported the utilization of excess of benign manganese(III) acetate to promote the reaction in DMF at elevated temperature ( Scheme 19 , method A) [ 39 ]. The same year, Yadav developed a catalytic system using silver nitrate as the catalyst and potassium persulfate as co-oxidant ( Scheme 19 , method B) [ 40 ].…”

Section: Nitrostyrenes In Denitrative C(sp 2 )-mentioning

confidence: 99%

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Denitrative Cross-Couplings of Nitrostyrenes

et al. 2020

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Interestingly, β-nitrostyrenes, typically bench stable compounds, are highly promising cross-coupling partners, due to their excellent availability and well understood reactivity. In this review, we report on the discovery and advancements, in the field of stereoselective, denitrative cross-couplings of β-nitrostyrenes with miscellaneous organic reagents. The rapidly expanding field offers alternative access to a broad range of functionalized alkenes, including β-alkylated styrenes, chalcones, stilbenes, cinnamic acids, and conjugated sulfones and phosphonates. The most important mechanistic pathways are briefly discussed, to familiarize readers with the elementary reactions occurring during the coupling.

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“…After oxidation, all obtained sulfones 4 were in the transconfiguration, assigned by comparison with previously reported data. [28][29][30][31][32][33][34]…”

Section: Syn Thesismentioning

confidence: 99%

Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts

Dong

2018

Synthesis

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A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert-butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.

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Mn(iii)-mediated regioselective synthesis of (E)-vinyl sulfones from sodium sulfinates and nitro-olefins

Abstract: A new efficient Mn(iii)-mediated coupling reaction of sodium sulfinates with nitro-olefins is described.

Cited by 39 publications

References 91 publications

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

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

Denitrative Cross-Couplings of Nitrostyrenes

Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts

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