Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes

被引：73

作者：

Chen, Zhengwang ^{[1
]}

Huang, Gao ^{[1
]}

Jiang, Huanfeng ^{[1
]}

Huang, Huawen ^{[1
]}

Pan, Xiaoyan ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 04期

基金：

中国国家自然科学基金;

关键词：

HIGHLY SUBSTITUTED FURANS; FUNCTIONALIZED CONJUGATED ENYNES; RING-OPENING CYCLOISOMERIZATION; ELECTRON-DEFICIENT ALKYNES; POT CYCLIZATION REACTION; C BOND FORMATION; POLYSUBSTITUTED FURANS; EFFICIENT SYNTHESIS; TETRASUBSTITUTED FURANS; DOMINO PROCESS;

D O I：

10.1021/jo1023987

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,5-Disubstituted 3-iodofurans are readily prepared under very mild reaction conditions by the palladium/copper-catalyzed cross-coupling of (Z)-beta-bromoenol acetates and terminal alkynes, followed by iodocyclization. The useful intermediates conjugated enyne acetates are obtained in high yields in the transformation. Aryl- and alkyl-substituted alkynes undergo iodocyclization in good yields. The resulting iodine-containing furans can be readily elaborated to 2,3,5-trisubstituted furans.

引用

页码：1134 / 1139

页数：6

共 110 条

[41] Tuning the Intramolecular Charge Transfer of Alkynylpyrenes: Effect on Photophysical Properties and Its Application in Design of OFF-ON Fluorescent Thiol Probes
Ji, Shaomin
Yang, Jun
Yang, Qing
Liu, Shasha
Chen, Maodu
Zhao, Jianzhang
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (13) : 4855 - 4865
[42] Iron-Catalyzed Domino Process for the Synthesis of α-Carbonyl Furan Derivatives via One-Pot Cyclization Reaction
Jiang, Huanfeng
Yao, Wenjuan
Cao, Hua
Huang, Huawen
Cao, Derong
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) : 5347 - 5350
[43] Synthesis of 2(3H)-Furanones via electrophilic Cyclization
Just, Ziwei W.
Larock, Richard C.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) : 2662 - 2667
[44] Keay B.A., 1997, Comprehensive Heterocyclic Chemistry II, V2, P395, DOI DOI 10.1016/B978-008096518-5.00047-2
[45] Synthesis of 2,3-disubstituted benzo[b]selenophenes via electrophilic cyclization
Kesharwani, T
Worlikar, SA
Larock, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) : 2307 - 2312
[46] Highly Substituted 2-Amido-furans From Rh(II)-Catalyzed Cyclopropenations of Ynamides
Li, Hongyan
Hsung, Richard P.
[J]. ORGANIC LETTERS, 2009, 11 (19) : 4462 - 4465
[47] Expedient Synthesis of Functionalized Conjugated Enynes: Palladium-Catalyzed Bromoalkynylation of Alkynes
Li, Yibiao
Liu, Xiaohang
Jiang, Huanfeng
Feng, Zhenning
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (19) : 3338 - 3341
[48] Palladium-Catalyzed Carbonylative Cycloisomerization of γ-Propynyl-1,3-diketones: A Concise Route to Polysubstituted Furans
Li, Yu
Yu, Zhengkun
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (22) : 8904 - 8907
[49] Tetrasubstituted Furans by PdII-Catalyzed Three-Component Domino Reactions of 2-(1-Alkynyl)-2-alken-1-ones with Nucleophiles and Vinyl Ketones or Acrolein
Liu, Renrong
Zhang, Junliang
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (37) : 9303 - 9306
[50] Synthetic Approach to Polysubstituted Furans: An Efficient Addition/Oxidative Cyclization of Alkynoates and 1,3-Dicarbonyl Compounds
Liu, Weibing
Jiang, Huanfeng
Zhang, Min
Qi, Chaorong
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (03) : 966 - 968

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