Nickel-Catalyzed Reaction between Vinyl Azides and an Alkyl Sulfonyl Radical Generated from DMSO: Rapid Access to β-Keto Sulfones

被引：10

作者：

Yang, Wen-Hui ^{[1
]}

Zhou, Yu ^{[1
]}

Tong, Ying ^{[1
]}

Wang, Zi-Ying ^{[1
]}

Wu, Hong-Li ^{[1
]}

Mei, Lan ^{[1
]}

Li, Qiang ^{[2
]}

Xie, Long-Yong ^{[1
,3
]}

Zhang, Jun-Qi ^{[4
,5
]}

Wei, Wen-Ting ^{[1
]}

机构：

[1] Ningbo Univ, Sch Mat Sci & Chem Engn, Ningbo 315211, Zhejiang, Peoples R China

[2] Liaocheng Univ, Sch Chem & Chem Engn, Shandong Prov Key Lab Chem Energy Storage & Novel, Liaocheng 252000, Peoples R China

[3] Hunan Univ Sci & Engn, Coll Chem & Bioengn, Yongzhou 425100, Hunan, Peoples R China

[4] Taizhou Univ, Adv Res Inst, Jiaojiang 318000, Peoples R China

[5] Taizhou Univ, Dept Chem, Jiaojiang 318000, Peoples R China

来源：

ACS SUSTAINABLE CHEMISTRY & ENGINEERING | 2024年 / 12卷 / 12期

基金：

中国国家自然科学基金;

关键词：

Green synthesis; Vinyl azides; Alkyl sulfonylradical; Dimethyl sulfoxide; ONE-POT; DIMETHYL-SULFOXIDE; SULFUR-DIOXIDE; METHYLATION; CONSTRUCTION; ENAMINES; REAGENT;

D O I：

10.1021/acssuschemeng.4c00574

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A sustainable method for the construction of valuable beta-keto sulfones lies in the reaction between vinyl azides and the alkyl sulfonyl radical generated from the low-cost and comparatively steady bulk chemical dimethyl sulfoxide (DMSO) that has been developed. This strategy features mild and economical reaction conditions using inexpensive NiCl2 as the catalyst and H2O2 as the green oxidant. The conversion occurs through a sequence of ordered processes consisting of a sulfonyl radical addition, denitrogen, hydrogen abstraction, and hydrolysis. Mechanistic studies indicate that sulfinic acid produced from DMSO plays an essential role in the reduction of Ni(III). The sensitivity assessment and gram-scale experiments proceed smoothly to demonstrate the robustness and practicality of this protocol.

引用

页码：5046 / 5051

页数：6

共 48 条

[1] AgN3-Catalyzed Hydroazidation of Terminal Alkynes and Mechanistic Studies [J].

Cao, Shanshan ;

Ji, Qinghe ;

Li, Huaizhi ;

Pang, Maolin ;

Yuan, Haiyan ;

Zhang, Jingping ;

Bi, Xihe .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (15) :7083-7091

[2] Facile Synthesis of -Keto Sulfones Employing Fenton's Reagent in DMSO [J].

Chalikidi, Petrakis N. ;

Uchuskin, Maxim G. ;

Trushkov, Igor V. ;

Abaev, Vladimir T. ;

Serdyuk, Olga V. .

SYNLETT, 2018, 29 (05) :571-575

[3] KI-mediated radical multi-functionalization of vinyl azides: a one-pot and efficient approach to β-keto sulfones and α-halo-β-keto sulfones [J].

Chen, Wenteng ;

Liu, Xingyu ;

Chen, En ;

Chen, Binhui ;

Shao, Jiaan ;

Yu, Yongping .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (06) :1162-1166

[4] Desulfonylation via Radical Process: Recent Developments in Organic Synthesis [J].

Chu, Xue-Qiang ;

Ge, Danhua ;

Cui, Yan-Ying ;

Shen, Zhi-Liang ;

Li, Chao-Jun .

CHEMICAL REVIEWS, 2021, 121 (20) :12548-12680

[5] Visible-light-mediated synthesis of β-keto sulfones using g-C3N4 as a recyclable photocatalyst under sustainable conditions [J].

Dam, Binoyargha ;

Sahoo, Ashish Kumar ;

Patel, Bhisma K. .

GREEN CHEMISTRY, 2022, 24 (18) :7122-7130

[6] Radical cyanomethylation via vinyl azide cascade-fragmentation [J].

Donald, James R. ;

Berrell, Sophie L. .

CHEMICAL SCIENCE, 2019, 10 (22) :5832-5836

[7] Phenanthroline-Initiated Anti-selective Hydrosulfonylation of Unactivated Alkynes with Sulfonyl Chlorides [J].

Dong, Ci-Shuang ;

Tong, Wen-Yan ;

Ye, Peng ;

Cheng, Nuoran ;

Qu, Shuanglin ;

Zhang, Bo .

ACS CATALYSIS, 2023, 13 (10) :6983-6993

[8] Vinyl Azides as Radical Acceptors in the Vitamin B12-Catalyzed Synthesis of Unsymmetrical Ketones [J].

Dworakowski, Krzysztof R. ;

Pisarek, Sabina ;

Hassan, Sidra ;

Gryko, Dorota .

ORGANIC LETTERS, 2021, 23 (23) :9068-9072

[9] THE REACTION OF OH RADICALS WITH DIMETHYL-SULFOXIDE - A COMPARATIVE-STUDY OF FENTON REAGENT AND THE RADIOLYSIS OF AQUEOUS DIMETHYL-SULFOXIDE SOLUTIONS [J].

EBERHARDT, MK ;

COLINA, R .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1071-1074

[10] Acid-Controlled Access to β-Sulfenyl Ketones and α,β-Disulfonyl Ketones by Pummerer Reaction of β-Keto Sulfones and Sulfoxides [J].

Fan, Jian ;

Zhao, Yiming ;

Zhang, Jitan ;

Xie, Meihua ;

Zhang, Yuzhong .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02) :691-701

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