Regio- and Stereoselective Synthesis of Ferrocene-Containing 尾-Iodoallylic Esters and Ethers from the Iodofunctionalization of Ferrocenylallene with Carboxylic Acids, Phenols, and Alcohols

详细信息    查看全文

• 作者：Shufeng Chen ; Hongli Zhang ; Qing Yan ; Chenjun Wang ; Fei Han ; Kaixin Zhang ; Haiying Zhao ; Baoguo Li
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：June 20, 2014
• 年：2014
• 卷：79
• 期：12
• 页码：5503-5510
• 全文大小：442K
• 年卷期：v.79,no.12(June 20, 2014)
• ISSN：1520-6904

文摘

The iodofunctionalization of ferrocenylallene with carboxylic acids, phenols, and alcohols is described. The reaction proceeds smoothly in the presence of molecule iodine as a halonium promoter and using various carboxylic acids, phenols, and alcohols as nucleophiles to give the corresponding ferrocene-containing 尾-iodoallylic ester and ether products in moderate to high yields and with high regio- and stereoselectivities. It can be envisaged that the regio- and stereoselectivity of this reaction may be controlled by the steric effect of the bulky ferrocene group. The presence of the C鈥揑 bond in the corresponding products makes these molecules highly attractive from a synthetic point of view, as it provides an opportunity for further transformations. Thus, palladium-catalyzed Heck coupling, Suzuki coupling, Sonogashira coupling, and copper-catalyzed click reactions were carried out successfully.