Palladium-Catalyzed Cascade Desulfitative Arylation of Acetylinic Oximes with Sodium Arylsulfinates

被引：4

作者：

Li, Jianxiao ^{[1
]}

Cen, Liying ^{[1
]}

He, Dan ^{[1
]}

Zhou, Daohao ^{[1
]}

Huang, Songxuan ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, 381 Wushan Rd, Guangzhou 510641, Guangdong, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 2022卷 / 20期

基金：

中国国家自然科学基金;

关键词：

Alkynes; Arylation; Annulation; Desulfurization; Palladium; ALKYNONE O-METHYLOXIMES; ISOXAZOLES; CYCLIZATION; RING; ALKENYLATION; HETEROCYCLES; ANNULATION; REACTIVITY;

D O I：

10.1002/ejoc.202200294

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein described a highly efficient palladium-catalyzed cascade desulfitative arylation of acetylinic oximes and sodium arylsulfinates with oxygen as the sole oxidant to access structurally diverse 4-aryl isoxazoles. This catalytic system exhibits mild conditions, broad substrate scope, and operational simplicity. Notably, other easily available aryl source substrates were perfectly tolerated in this catalytic system, thus providing a promising application in synthetic and pharmaceutical chemistry.

引用

页数：5

共 50 条

[41] Palladium-Catalyzed α-Arylation Reactions in Total Synthesis [J].

Sivanandan, Sudheesh T. ;

Shaji, Ashna ;

Ibnusaud, Ibrahim ;

Seechurn, Carin C. C. Johansson ;

Colacot, Thomas J. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (01) :38-49

[42] Palladium(II)-Catalyzed Desulfitative Synthesis of Aryl Ketones from Sodium Arylsulfinates and Nitriles: Scope, Limitations, and Mechanistic Studies [J].

Skillinghaug, Bobo ;

Skold, Christian ;

Rydfjord, Jonas ;

Svensson, Fredrik ;

Behrends, Malte ;

Savmarker, Jonas ;

Sjoberg, Per J. R. ;

Larhed, Mats .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (24) :12018-12032

[43] Palladium-catalyzed arylation of α,β-unsaturated Weinreb amides [J].

Kim, Ko Hoon ;

Lee, Sangku ;

Kim, Se Hee ;

Lim, Cheol Hee ;

Kim, Jae Nyoung .

TETRAHEDRON LETTERS, 2012, 53 (38) :5088-5093

[44] Palladium-Catalyzed β-Arylation of Cyclic α,β-Unsaturated O-Methyl Oximes with Aryl Iodides [J].

Akagi, Yusuke ;

Fukuyama, Shiori ;

Komatsu, Toshiya .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2020, 68 (03) :288-291

[45] Palladium-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Sodium Arylsulfinates [J].

Li, Yue ;

Yang, Wen ;

Cheng, Guo ;

Yang, Dingqiao .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11) :4744-4750

[46] Advances in Palladium-Catalyzed Cascade Cyclizations [J].

Biemolt, Jasper ;

Ruijter, Eelco .

ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (20) :3821-3871

[47] Palladium-Catalyzed Cascade Annulation To Construct Functionalized β- and γ-Lactones in Ionic Liquids [J].

Li, Jianxiao ;

Yang, Wanfei ;

Yang, Shaorong ;

Huang, Liangbin ;

Wu, Wanqing ;

Sun, Yadong ;

Jiang, Huanfeng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (28) :7219-7222

[48] Cascade Palladium-Catalyzed Direct Intramolecular Arylation/Alkene Isomerization Sequences: Synthesis of Indoles and Benzofurans [J].

Yagoubi, Myriam ;

Cruz, Ana C. F. ;

Nichols, Paula L. ;

Elliott, Richard L. ;

Willis, Michael C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (43) :7958-7962

[49] Recent Developments in Palladium-Catalyzed Oxidative Cascade Carbocyclization [J].

Zhang, Di ;

Liu, Jianguo ;

Cordova, Armando ;

Liao, Wei-Wei .

ACS CATALYSIS, 2017, 7 (10) :7051-7063

[50] Construction of a Protoberberine Alkaloid Skeleton via the Palladium-Catalyzed α-Arylation-Amide Formation Cascade [J].

Li, Shaofeng ;

Nie, Hanyu ;

Duan, Mengyan ;

Wang, Wenfei ;

Zhu, Congjun ;

Song, Chuanjun .

ORGANIC LETTERS, 2021, 23 (24) :9631-9634

← 1 2 3 4 5 →