Preparation of aromatic γ-hydroxyketones by means of Heck coupling of aryl halides and 2,3-dihydrofuran, catalyzed by a palladium(ii) glycine complex under microwave irradiation

被引：2

作者：

Jimenez-Cruz, Juan C. ^{[1
]}

Guzman-Mejia, Ramon ^{[1
]}

Juaristi, Eusebio ^{[2
,3
]}

Sanchez-Antonio, Omar ^{[2
]}

Garcia-Revilla, Marco A. ^{[4
]}

Betzabe Gonzalez-Campos, J. ^{[1
]}

Avina-Verduzco, Judit ^{[1
]}

机构：

[1] Univ Michoacana, Inst Invest Quim Biol, Edificio B-1,Planta Baja Ciudad Univ, Morelia 58030, Michoacan, Mexico

[2] Ctr Invest & Estudios Avanzados, Dept Quim, Ave Inst Politecn,Nacl 2508, Ciudad De Mexico 07360, Mexico

[3] Colegio Nacl, Donceles 104, Ciudad De Mexico 06020, Mexico

[4] Univ Guanajuato, Dept Quim, Noria Alta S-N, Guanajuato 36050, Gto, Mexico

来源：

NEW JOURNAL OF CHEMISTRY | 2020年 / 44卷 / 31期

关键词：

ELECTROSPRAY-IONIZATION MASS; BAYLIS-HILLMAN REACTION; OXIDATIVE ADDITION; BACCATIN-III; ARYLATION; MECHANISM; CONVENIENT; EFFICIENT; CHEMISTRY; EPIBATIDINE;

D O I：

10.1039/d0nj02630a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of aromatic gamma-hydroxyketones were prepared by means of Heck coupling reaction of aryl halides and 2,3-dihydrofuran, catalyzed by PdCl2 center dot Gly(2)and under microwave irradiation. This synthetic transformation involves the formation of an aryl-dihydrofuranoic intermediate, followed by an unusual opening of the heterocycle promoted by a water molecule and the formation of the ketone carbonyl function through keto-enol tautomerism.

引用

页码：13382 / 13392

页数：11

共 7 条

[1] Heterogeneously Catalyzed Phosphine-Free Heck Cross-Coupling Reaction of Aryl Halides with Reusable Palladium(II) Schiff Base Complex
Islam, Manirul
Mondal, Paramita
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2011, 22 (02) : 319 - 326
[2] Microwave-promoted Suzuki-Miyaura cross-coupling of aryl halides with phenylboronic acid under aerobic conditions catalyzed by a new palladium complex with a thiosemicarbazone ligand
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TETRAHEDRON LETTERS, 2006, 47 (26) : 4403 - 4407
[3] Synthesis of functionalized aryl-alkenes catalyzed by CN-ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime under microwave irradiation
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IRANIAN JOURNAL OF CATALYSIS, 2015, 5 (01): : 21 - 31
[4] Dimeric ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime catalyzed Suzuki–Miyaura cross-coupling reaction under microwave irradiation
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Journal of the Iranian Chemical Society, 2015, 12 : 1177 - 1181
[5] Dimeric ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime catalyzed Suzuki-Miyaura cross-coupling reaction under microwave irradiation
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JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2015, 12 (07) : 1177 - 1181
[6] The first preparation of 4-substituted 1,2-oxaborol-2(5H)-ols and their palladium-catalyzed cross-coupling with aryl halides to prepare stereodefined 2,3-disubstituted allyl alcohols
Fang, GH
Yan, ZJ
Yang, J
Deng, MZ
SYNTHESIS-STUTTGART, 2006, (07): : 1148 - 1154
[7] Copper- and solvent-free Sonogashira coupling reactions of aryl halides with terminal alkynes catalyzed by 1-phenyl-1,2-propanedione-2-oxime thiosemi-carbazone-functionalized polystyrene resin supported Pd(II) complex under aerobic conditions
Bakherad, Mohammad
Keivanloo, Ali
Bahramian, Bahram
Jajarmi, Saeedeh
APPLIED CATALYSIS A-GENERAL, 2010, 390 (1-2) : 135 - 140

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