Nickel-Catalyzed Desulfonylative Reductive Cross-Coupling of Aryl Sulfones with Aryl Bromides

被引：14

作者：

Huang, Xinmiao ^{[1
,2
]}

Tang, Ling ^{[1
,2
]}

Song, Zhiyong ^{[1
,2
]}

Jiang, Shuangshuang ^{[1
,2
]}

Liu, Xianmao ^{[1
,2
]}

Ma, Ming ^{[1
,2
]}

Chen, Bo ^{[1
,2
]}

Ma, Yuanhong ^{[1
,2
]}

机构：

[1] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Phytochemistry R&D Hunan Prov, Key Lab Chem Biol & Tradit Chinese Med Res,Minist, Changsha 410081, Peoples R China

[2] Hunan Normal Univ, Coll Chem & Chem Engn, Key Lab Assembly & Applicat Organ Funct Mol Hunan, Changsha 410081, Peoples R China

来源：

ORGANIC LETTERS | 2023年

基金：

中国国家自然科学基金;

关键词：

SULFIDES; HALIDES; BONDS;

D O I：

10.1021/acs.orglett.3c00185

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, a nickel catalysis system for desulfonylative C(sp(2))-C(sp(2)) reductive cross-coupling reactions of aryl sulfone derivatives with a range of aryl bromides has been established to form diverse biaryl compounds. The complex Ar-Ni(II)-SO(2)CF3 bearing a phosphine ligand through oxidative addition of aryl sulfone to Ni(0) species was isolated and confirmed by an X-ray, which provides solid evidence for the understanding of the C(Ar)-SO2 bond activation and reaction mechanism.

引用

收藏

页码：1198 / 1203

页数：6

相关论文

共 38 条

[11] Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones To Prepare C-Aryl Glycals and Acyclic Vinyl Ethers [J].

Gong, Liang ;

Sun, Hong-Bao ;

Deng, Li-Fan ;

Zhang, Xia ;

Liu, Jie ;

Yang, Shengyong ;

Niu, Dawen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (19) :7680-7686

[12] Ni-catalyzed C-S bond construction and cleavage [J].

Huang, Su ;

Wang, Ming ;

Jiang, Xuefeng .

CHEMICAL SOCIETY REVIEWS, 2022, 51 (19) :8351-8377

[13] A General, Multimetallic Cross-Ullmann Biheteroaryl Synthesis from Heteroaryl Halides and Heteroaryl Triflates [J].

Kang, Kai ;

Loud, Nathan L. ;

DiBenedetto, Tarah A. ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (51) :21484-21491

[14] Sulfonate Versus Sulfonate: Nickel and Palladium Multimetallic Cross-Electrophile Coupling of Aryl Triflates with Aryl Tosylates [J].

Kang, Kai ;

Huang, Liangbin ;

Weix, Daniel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (24) :10634-10640

[15] Full-Spectrum Fluoromethyl Sulfonation via Modularized Multicomponent Coupling [J].

Li, Kejie ;

Wang, Ming ;

Jiang, Xuefeng .

CCS CHEMISTRY, 2022, 4 (05) :1526-1534

[16] Transition-metal mediated carbon-sulfur bond activation and transformations: an update [J].

Lou, Jiang ;

Wang, Quannan ;

Wu, Ping ;

Wang, Hongmei ;

Zhou, Yong-Gui ;

Yu, Zhengkun .

CHEMICAL SOCIETY REVIEWS, 2020, 49 (13) :4307-4359

[17] Heterocyclic Allylsulfones as Latent Heteroaryl Nucleophiles in Palladium-Catalyzed Cross-Coupling Reactions [J].

Markovic, Tim ;

Murray, Philip R. D. ;

Rocke, Benjamin N. ;

Shavnya, Andre ;

Blakemore, David C. ;

Willis, Michael C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (46) :15916-15923

[18] Vinyl sulfones: Synthetic preparations and medicinal chemistry applications [J].

Meadows, D. Christopber ;

Gervay-Hague, Jacquelyn .

MEDICINAL RESEARCH REVIEWS, 2006, 26 (06) :793-814

[19] Modular radical cross-coupling with sulfones enables access to sp3-rich (fluoro)alkylated scaffolds [J].

Merchant, Rohan R. ;

Edwards, Jacob T. ;

Qin, Tian ;

Kruszyk, Monika M. ;

Bi, Cheng ;

Che, Guanda ;

Bao, Deng-Hui ;

Qiao, Wenhua ;

Sun, Lijie ;

Collins, Michael R. ;

Fadeyi, Olugbeminiyi O. ;

Gallego, Gary M. ;

Mousseau, James J. ;

Nuhant, Philippe ;

Baran, Phil S. .

SCIENCE, 2018, 360 (6384) :75-80

[20] Nickel-Catalyzed Reductive 2-Pyridination of Aryl Iodides with Difluoromethyl 2-Pyridyl Sulfone [J].

Miao, Wenjun ;

Ni, Chuanfa ;

Xiao, Pan ;

Jia, Rulong ;

Zhang, Wei ;

Hu, Jinbo .

ORGANIC LETTERS, 2021, 23 (03) :711-715

← 1 2 3 4 →