Palladium-Catalyzed Oxidative Annulation of Acrylic Acid and Amide with Alkynes: A Practical Route to Synthesize α-Pyrones and Pyridones

被引：63

作者：

Yu, Yue ^{[1
]}

Huang, Liangbin ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 08期

基金：

中国国家自然科学基金;

关键词：

AEROBIC INTERMOLECULAR CYCLIZATION; OXO GOLD CARBENES; C-H ACTIVATION; BENZOIC-ACIDS; GAMMA; DERIVATIVES; ALKENES; BONDS; BETA; ACETOXYPALLADATION;

D O I：

10.1021/ol500611d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A range of internal alkynes smoothly underwent palladium-catalyzed oxidative annulations with acrylic acid and amide to afford alpha-pyrones and pyridones in good to excellent yields with high regioselectivity. The usage of O-2 (1 atm) as a stoichiometric oxidant with H2O as the only byproduct under mild conditions makes this process more attractive and practical.

引用

页码：2146 / 2149

页数：4

共 50 条

[41] Palladium-Catalyzed Synthesis of Fluorescent Benzo[4,5]imidazo[1,2-a]pyridines through Annulation Reaction of Benzimidazoles and Alkynyl Bromides with Internal Alkynes
Chen, Xin
Sun, Peng
Mo, Baichuan
Chen, Chunxia
Peng, Jinsong
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01) : 352 - 366
[42] Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom Economic Synthesis of 1,4-Dicarboxylic Acid Diesters
Liu, Jiawang
Dong, Kaiwu
Franke, Robert
Neumann, Helfried
Jackstell, Ralf
Beller, Matthias
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (32) : 10282 - 10288
[43] Synthesis of Dihydrophosphaisocoumarins through a Palladium-Catalyzed Oxidative Cyclization of Arylphosphonic Acid Monoethyl Esters with 1,3-Dienes
Son, Jeong-Yu
Kim, Hyunseok
Jeon, Woo Hyung
Baek, Yonghyeon
Seo, Boram
Um, Kyusik
Lee, Kooyeon
Lee, Phil Ho
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (18) : 3194 - 3206
[44] Synthesis of Azulenopyridinones through Palladium-Catalyzed Oxidative [4+2] Cyclization Reactions ofN-Methoxyazulene-1-and 2-carboxamides with Alkynes
Han, Gi Uk
Son, Jeong-Yu
Park, Dahee
Eom, Hyeonsik
Lee, Kyungsup
Noh, Hee Chan
Lee, Kooyeon
Lee, Phil Ho
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4749 - 4754
[45] Cobalt-Catalyzed Oxidative Annulation of Nitrogen-Containing Arenes with Alkynes: An Atom-Economical Route to Heterocyclic Quaternary Ammonium Salts
Prakash, Sekar
Muralirajan, Krishnamoorthy
Cheng, Chien-Hong
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (05) : 1844 - 1848
[46] Palladium-Catalyzed 8-Aminoquinoline-Aided sp2 δ-C-H Intramolecular Amidation/Annulation: A Route to Tricyclic Quinolones
Padmavathi, Rayavarapu
Babu, Srinivasarao Arulananda
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (06) : 899 - 908
[47] Palladium-Catalyzed Base-Promoted Arylation of Unactivated C(sp3)-H Bonds by Aryl Iodides: A Practical Approach To Synthesize β-Aryl Carboxylic Acid Derivatives
Gou, Quan
Liu, Gang
Zhou, Lanxiu
Chen, Suiyun
Qin, Jun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (42) : 6314 - 6318
[48] Palladium-catalyzed arylations in 4-pyrone systems: 2,6-diaryl-3,5-dibromo-4-pyrones and kojic acid
Ghasemi, Zarrin
Mejarshin, Fatemeh Poorhossain
Fathi, Zahra
Shahrisa, Aziz
MONATSHEFTE FUR CHEMIE, 2016, 147 (06): : 1107 - 1111
[49] Palladium-Catalyzed Carbonylative [3+2+1] Annulation of N-Aryl-Pyridine-2-Amines with Internal Alkynes by C-H Activation: Facile Synthesis of 2-Quinolinones
Chen, Jianbin
Natte, Kishore
Spannenberg, Anke
Neumann, Helfried
Beller, Matthias
Wu, Xiao-Feng
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (44) : 14189 - 14193
[50] Practical Synthesis of 2-Arylacetic Acid Esters via Palladium-Catalyzed Dealkoxycarbonylative Coupling of Malonates with Aryl Halides
Song, Bingrui
Rudolphi, Felix
Himmler, Thomas
Goossen, Lukas J.
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (09) : 1565 - 1574

← 1 2 3 4 5 →