Palladium-catalyzed tandem reaction of yne-propargylic carbonates with boronic acids: A simple method for the synthesis of fused aromatic rings through allene-mediated electrocyclization

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	Palladium-catalyzed tandem reaction of yne-propargylic carbonates with boronic acids: A simple method for the synthesis of fused aromatic rings through allene-mediated electrocyclization
	Wang F(王峰) ; Tong XF(童晓峰) ; Cheng J(成奖) ; Zhang ZG(张兆国)
刊名	Chem.-Eur. J.
	2004
卷号	10 期号:21 页码:5338-5344
ISSN号	0947-6539
其他题名	钯催化的炔-丙炔醇碳酸酯与硼酸的串联反应: 通过联烯促进的电环化反应合成芳香并环化合物的方法
通讯作者	张兆国
英文摘要	The palladium-catalyzed tandem reactions of yne-propargylic carbonates with aryl boronic acids, 2-furyl boronic acid, and 2-thiopheneboronic acid, followed by 6pi-electrocyclization to give fused ring aromatic products such as naphthalene, benzofuran, and benzothiophene derivatives are realized. Screening of the reaction conditions revealed that the combination of [Pd(PPh3)(4)] in THF gave the best results in terms of reactivity and product yields in the reaction of yne-propargylic carbonates with phenylboronic acid. The reaction is sensitive toward steric hindrance when substituted phenylboronic acids are emplyed. However, when we take 2-furyl boronic acid as the organometallic reagent, most substrates perform very well to give benzofuran derivatives. In addition, 2-thiopheneboronic acid is also a very effective coupling reagent to give bezothiophenes in high yields. A mechanism is proposed that involves the formation of an allenylpalladium complex from Pd-0 and propargylic carbonate, followed by insertion of an intramolecular triple bond and the Suzuki coupling reaction, and then electrocyclization.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/chem.200400573
语种	英语
WOS记录号	WOS:000224783800008
公开日期	2013-08-14
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/27609]
专题	上海有机化学研究所_上海有机化学研究所
推荐引用方式 GB/T 7714	Wang F,Tong XF,Cheng J,et al. Palladium-catalyzed tandem reaction of yne-propargylic carbonates with boronic acids: A simple method for the synthesis of fused aromatic rings through allene-mediated electrocyclization[J]. Chem.-Eur. J.,2004,10(21):5338-5344.
APA	王峰,童晓峰,成奖,&张兆国.(2004).Palladium-catalyzed tandem reaction of yne-propargylic carbonates with boronic acids: A simple method for the synthesis of fused aromatic rings through allene-mediated electrocyclization.Chem.-Eur. J.,10(21),5338-5344.
MLA	王峰,et al."Palladium-catalyzed tandem reaction of yne-propargylic carbonates with boronic acids: A simple method for the synthesis of fused aromatic rings through allene-mediated electrocyclization".Chem.-Eur. J. 10.21(2004):5338-5344.