Nickel-catalysed C-N cross-coupling of organoboronic acids and isoxazoles

被引：1

作者：

Zhao, Yupeng ^{[1
]}

Wu, Changshu ^{[1
]}

Zhang, Jiaming ^{[1
]}

Gao, Yang ^{[1
,2
]}

Yuan, Zhuoxuan ^{[1
]}

Li, Xianwei ^{[1
]}

Chen, Qian ^{[1
]}

Huo, Yanping ^{[1
,2
]}

机构：

[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

[2] Guangdong Lab, Jieyang Branch Chem & Chem Engn, Jieyang 515200, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 18期

基金：

中国国家自然科学基金;

关键词：

INTERMOLECULAR HYDROAMINATION; ASYMMETRIC HYDROGENATION; EFFICIENT SYNTHESIS; AMIDES; HALIDES; ALKYNES; ISOMERIZATION; ENAMINONES; ALKENES;

D O I：

10.1039/d4qo01050g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A nickel-catalysed C-N cross-coupling of organoboronic acids and isoxazoles has been established for the efficient synthesis of (Z) N-aryl beta-enamino esters. 5-Alkoxy/phenoxy isoxazoles serve as reliable aminating reagents in this transformation through N-O bond cleavage. A wide range of N-aryl beta-enamino esters (32 examples in up to 93% yields) with different functional groups were synthesized through this method under mild reaction conditions. A nickel-catalyzed C-N cross-coupling of organoboronic acids and isoxazoles has been established for the efficient synthesis of (Z) N-aryl beta-enamino esters.

引用

页码：5138 / 5143

页数：6

共 50 条

[21] N-Alkoxyphthalimides as Nitrogen Electrophiles to Construct C-N Bonds via Reductive Cross-Coupling [J].

Wu, Kang ;

Wang, Tian-Zhang ;

Zhang, Chao-Peng ;

Guan, Yu-Qiu ;

Liang, Yu-Feng .

JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (14) :10004-10011

[22] Efficient cobalt-catalyzed C-N cross-coupling reaction between benzamide and aryl iodide in water [J].

Tan, Bryan Yong-Hao ;

Teo, Yong-Chua .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (38) :7478-7481

[23] Nickel-Catalyzed Migratory Cross-Coupling Reactions: New Opportunities for Selective C-H Functionalization [J].

Wang, You ;

He, Yuli ;

Zhu, Shaolin .

ACCOUNTS OF CHEMICAL RESEARCH, 2023, 56 (23) :3475-3491

[24] A New, Efficient and Recyclable Lanthanum(III) Oxide-Catalyzed C-N Cross-Coupling [J].

Murthy, S. Narayana ;

Madhav, B. ;

Reddy, V. Prakash ;

Nageswar, Y. V. D. .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (18) :3241-3245

[25] Mechanochemical Generation of Active Pd/BippyPhos Catalyst for Efficient C-N Cross-Coupling in Air [J].

Karabiyikli, Deniz ;

Saad, Alexandre ;

Hammoud, Sokaina ;

Schneider, Severine ;

Manca, Romuald ;

Raya, Jesus ;

Schmitt, Martine ;

Bihel, Frederic .

CHEMSUSCHEM, 2025,

[26] Amide/Ester Cross-Coupling via C-N/C-H Bond Cleavage: Synthesis of β-Ketoesters [J].

Chen, Jiajia ;

Joseph, Devaneyan ;

Xia, Yuanzhi ;

Lee, Sunwoo .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (08) :5943-5953

[27] Cross-Coupling of Organolithium with Ethers or Aryl Ammonium Salts by C-O or C-N Bond Cleavage [J].

Yang, Ze-Kun ;

Wang, Dong-Yu ;

Minami, Hiroki ;

Ogawa, Hiroyuki ;

Ozaki, Takashi ;

Saito, Tatsuo ;

Miyamoto, Kazunori ;

Wang, Chao ;

Uchiyama, Masanobu .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (44) :15693-15699

[28] Sequential Organozinc Formation and Negishi Cross-Coupling of Amides Catalysed by Cobalt Salt [J].

Dorval, Celine ;

Dubois, Elodie ;

Bourne-Branchu, Yann ;

Gosmini, Corinne ;

Danoun, Gregory .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (08) :1777-1780

[29] Asymmetric Nickel-Catalysed Cross-Hydrovinylation of Two Terminal Alkenes [J].

Hilt, Gerhard .

CHEMCATCHEM, 2015, 7 (11) :1639-1641

[30] Nickel-Catalyzed C-N Cross-Coupling of Ammonia, (Hetero)anilines, and Indoles with Activated (Hetero)aryl Chlorides Enabled by Ligand Design [J].

McGuire, Ryan T. ;

Paffile, Julia F. J. ;

Zhou, Yuqiao ;

Stradiotto, Mark .

ACS CATALYSIS, 2019, 9 (10) :9292-9297

← 1 2 3 4 5 →