Deaminative metal-free reaction of alkenylboronic acids, sodium metabisulfite and Katritzky salts

Zhu, Tong‐Hao; Jia, Shen; Sun, Yuyuan; Wu, Jie

doi:10.1039/d0cc07632e

Cited by 24 publications

(36 citation statements)

References 78 publications

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“…The Wu group and the Feng group reported the synthesis of vinylsulfones from styrenes under copper catalysis and TBAI/TBHP conditions respectively [12] . In an another report, the Wu group developed a metal‐free, three‐component coupling of vinylboronic acid, Na 2 S 2 O 5 and Katritzky salt as alkyl radical source [13] . Arylvinylsulfone can also be achieved from 2‐bromovinylbenzene and sodium arylsulfinate salt by copper catalysed or metal‐free condition [14] .…”

Section: Figurementioning

confidence: 99%

“…4,4'-sulfonylbis(methoxybenzene), (3 e). [20] Column chromatography (SiO 2 , eluting with 80 : 20 hexane/ethyl acetate) afforded the desired product as a white solid (111.2 mg, 80% 13 C NMR (100 MHz, CDCl 3 ): δ 163.9, 146.0 (q, J = 1.2 Hz), 134.6 (q, J = 33.0 Hz), 132.0, 130.2, 127.9, 126.4 (q, J = 3.8 Hz), 123.2 (q, J = 271.6 Hz), 114.8, 55.8; 19 F NMR (376 MHz, CDCl 3 ): δ À 63.12.…”

Section: -(Tert-butyl)-4-((4-methoxyphenyl)sulfonyl)benzene (3 D)mentioning

confidence: 99%

“…[23] Column chromatography (SiO 2 , eluting with 80 : 20 hexane/ethyl acetate) afforded the desired product as a white solid (76.2 mg, 60%). 1 H NMR (400 MHz, CDCl 3 ): δ 8.02 (dd, J 1 = 2.8 Hz, J 2 = 1.2 Hz, 1H), 7.88 (d, J = 8.8 Hz, 2H), 7.36-7.34 (m, 1H), 7.29 (dd, J 1 = 5.2 Hz, J 2 = 1.2 Hz, 1H), 6.96 (d, J = 9.2 Hz, 2H), 3.84 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 163. 5, 142.9, 133.2, 130.8, 129.8, 128.3, 125.7, 114.6, 55.7. 2-((4-nitrophenyl)sulfonyl)naphthalene, (3 u).…”

Section: -((4-methoxyphenyl)sulfonyl)naphthalene (3 S) [5e]mentioning

confidence: 99%

“…128-130 °C. 1 H NMR (400 MHz, CDCl 3 ): δ 8.51 (s, 1H), 7.96 (d, J = 7.2 Hz, 1H), 7.90 (d, J = 8.8 Hz, 1H), 7.85 (d, J = 7.6 Hz, 1H), 7.81 (dd, J 1 = 8.4 Hz, J 2 = 1.6 Hz, 1H), 7.63-7.57 (m, 3H), 7.36 (d, J = 2.0 Hz, 1H), 6.86 (d, J = 8.4 Hz, 1H), 6.01(s, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 151.9, 148.5, 138.9, 135.0, 135.0, 132.3, 129.6, 129.4, 129.1, 128.7, 127.9, 127.7, 123.7, 122.6, 108.6, 107.9, 102.4; HRMS (EI, m/z) calcd. For C 17 H 12 O 4 S, M: 312.0456; found: 312.0456. methyl(2-(naphthalen-2-ylsulfonyl)phenyl)sulfane, (3 ab).…”

Section: -(Naphthalen-2-ylsulfonyl)benzo[d][13]dioxole (3 Aa)mentioning

confidence: 99%

“…1 H NMR (400 MHz, CDCl 3 ): δ 8.80 (d, J = 2.4 Hz, 1H), 8.54 (s, 1H), 8.03 (dd, J 1 = 8.8 Hz, J 2 = 2.8 Hz, 1H), 7.97 (d, J = 7.6 Hz, 1H), 7.93 (d, J = 8.4 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7. 1H),2H),7.77 (d,J = 8.8 Hz,1H), 3.95 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 166. 8, 148.3, 138.6, 137.7, 135.1, 132.3, 131.1, 129.9, 129.5, 129.3, 128.9, 128.0, 127.8, 122.4, 111.7, 54.4; HRMS (EI, m/z) calcd.…”

Section: -Methoxy-5-(naphthalen-2-ylsulfonyl)pyridine (3 Af)mentioning

confidence: 99%

See 4 more Smart Citations

Aryldiazonium Salts and DABSO: A Versatile Combination for Three‐Component Sulfonylative Cross‐Coupling Reactions

Das

Jana

2022

Chemistry An Asian Journal

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A combination of aryldiazonium salts and DABSO provides a unique opportunity for sulfonylative multicomponent cross‐coupling reactions. Here, a copper‐catalyzed three‐component cross‐coupling of aryldiazonium salts, DABSO with arylboronic acids to obtain medicinally relevant unsymmetrical diarylsulfones is disclosed. Interestingly, a catalyst‐free approach for the synthesis of arylvinylsulfones from the corresponding vinyl boronic acids or vinyl halides is explored under basic condition. Tethered aryldiazonium salts provided the corresponding annulated alkylvinylsulfones via alkene difunctionalization under the same transition metal‐free condition. Mechanistically, these multicomponent reactions proceed through a single electron pathway by the formation of arylsulfonyl radical as a key intermediate.

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Section: Figurementioning

confidence: 99%

Section: -(Tert-butyl)-4-((4-methoxyphenyl)sulfonyl)benzene (3 D)mentioning

confidence: 99%

Section: -((4-methoxyphenyl)sulfonyl)naphthalene (3 S) [5e]mentioning

confidence: 99%

Section: -(Naphthalen-2-ylsulfonyl)benzo[d][13]dioxole (3 Aa)mentioning

confidence: 99%

Section: -Methoxy-5-(naphthalen-2-ylsulfonyl)pyridine (3 Af)mentioning

confidence: 99%

See 3 more Smart Citations

Aryldiazonium Salts and DABSO: A Versatile Combination for Three‐Component Sulfonylative Cross‐Coupling Reactions

Das

Jana

2022

Chemistry An Asian Journal

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Metal‐Free Multi‐Component Sulfur Dioxide Insertion Reaction Leading to Quinoxalin‐2‐One‐Containing Vinyl Sulfones under Visible‐Light Photoredox Catalysis

Luo

Lin

et al. 2021

Adv Synth Catal

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A metal‐free multi‐component sulfur dioxide insertion reaction of alkynes, sodium metabisulfite, aryldiazonium, and quinoxalin‐2‐ones has been developed under visible‐light photoredox‐catalysis. This photocatalytic tandem reaction would be conducted at room temperature by using of Rhodamine 6G as organic photocatalyst and sodium metabisulfite as the SO2 surrogate. This protocol provides a synthetic strategy for the construction of various quinoxalin‐2‐one‐containing vinyl sulfones with favourable functional group tolerance, in which one C−C bond and two C−S bonds were constructed in one pot procedure.

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Three‐Component Vicinal Sulfonamination of Alkynes toward 3‐Sulfonylindoles via the Insertion of Sulfur Dioxide

Zhang²,

Chen³

et al. 2021

Asian J Org Chem

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A convenient and efficient three‐component transformation of 2‐alkynyl arylazides, aryldiazonium tetrafluoroborates and sodium metabisulfite has been developed under mild and transition‐metal‐free conditions. Sodium metabisulfite which is cheap, easily available and abundant in nature is successfully utilized as SO2 surrogate, leading to a series of 3‐sulfonylindole derivatives in moderate to good yields. Cascade radical addition/cyclization was involved in this protocol with the formation of two C−S bonds and one C−N bond in one‐pot.

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Deaminative metal-free reaction of alkenylboronic acids, sodium metabisulfite and Katritzky salts

Cited by 24 publications

References 78 publications

Aryldiazonium Salts and DABSO: A Versatile Combination for Three‐Component Sulfonylative Cross‐Coupling Reactions

Aryldiazonium Salts and DABSO: A Versatile Combination for Three‐Component Sulfonylative Cross‐Coupling Reactions

Metal‐Free Multi‐Component Sulfur Dioxide Insertion Reaction Leading to Quinoxalin‐2‐One‐Containing Vinyl Sulfones under Visible‐Light Photoredox Catalysis

Three‐Component Vicinal Sulfonamination of Alkynes toward 3‐Sulfonylindoles via the Insertion of Sulfur Dioxide

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