Efficient and Functional-Group-Tolerant Synthesis of Substituted Furans through the Pd-Catalyzed 5-exo-dig Cyclization/Coupling of γ-Acetylenic β-Keto Esters with (Hetero)Aryl Bromides

被引：4

作者：

Kolodziejczyk, Agata ^{[1
]}

Chaladaj, Wojciech ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 2018卷 / 20-21期

关键词：

Oxygen heterocycles; Palladium; Homogeneous catalysis; Cyclization; Synthetic methods; ONE-POT SYNTHESIS; ALLYLIDENE CYCLOPENTANES; ORGANIC HALIDES; PALLADIUM; CYCLOISOMERIZATION; CONSTRUCTION; CASCADE; ALKYNES;

D O I：

10.1002/ejoc.201800046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report an efficient protocol for the synthesis of 2,3,5-trisubstituted furans through the reaction of readily available -acetylenic -keto esters with aryl and heteroaryl bromides. The reaction, which involves a 5-exo-dig cyclization, coupling, and isomerization of a double bond, proceeds smoothly with very low catalyst loading (0.1 mol-%), and shows excellent functional-group tolerance.

引用

页码：2554 / 2560

页数：7

共 6 条

[1] Pd-catalyzed 5-exo-dig cyclization/etherification cascade of N-propargyl arylamines for the synthesis of polysubstituted furans
Li, Meng-Ru
Zheng, Meng-Yao
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CHEMICAL COMMUNICATIONS, 2024, 60 (60) : 7721 - 7724
[2] Functional-Group-Tolerant Pd-Catalyzed Carbonylative Negishi Coupling with Aryl Iodides
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[3] Tandem Pd-Catalyzed Cyclization/Coupling of Non-Terminal Acetylenic Activated Methylenes with (Hetero)Aryl Bromides
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MOLECULES, 2022, 27 (03):
[4] Lithium Enables Pd-Catalyzed 5-endo-dig Cyclization/Coupling of α-Homopropargyl-β-ketoesters with Aryl Bromides and Triflates
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ORGANIC LETTERS, 2024, 26 (39) : 8254 - 8259
[5] Cu-Mn spinel oxide catalyzed synthesis of imidazo[1,2-a]pyridines through domino three-component coupling and 5-exo-dig cyclization in water
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Guru, Santosh K.
Jain, Shreyans K.
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Singh, Baldev
Bharate, Sandip B.
Vishwakarma, Ram A.
RSC ADVANCES, 2013, 3 (43): : 20869 - 20876
[6] A Simple and Efficient One-Pot Synthesis of Substituted Benzo[b]furans by Sonogashira Coupling-5-endo-dig Cyclization Catalyzed by Palladium Nanoparticles in Water Under Ligand- and Copper-Free Aerobic Conditions
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Dey, Raju
Ranu, Brindaban C.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (31) : 6067 - 6071

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