Oxidative Ring Closure and Metal Triggered Ring Opening: Syntheses of Macrocyclic and Linear Hexapyrroles

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• 作者：Kai Zhang ; Pingchun Wei ; Xin Li ; Hans 脜gren ; Yongshu Xie
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：December 19, 2014
• 年：2014
• 卷：16
• 期：24
• 页码：6354-6357
• 全文大小：301K
• ISSN：1523-7052

文摘

A C₆F₅-substituted hexapyrrane (1) was synthesized in one step. Oxidative cyclization of 1 with DDQ afforded a phlorin鈥揹ipyrrin conjugate (2), and subsequent FeCl₃-assisted oxidative cleavage of 2 afforded a terminally di-伪-methoxy substituted hexapyrrin (3). On the other hand, oxidation of 1 with FeCl₃ afforded 3, a hexapyrrinone Fe³⁺ complex (4), and a hexaphyrin (1,1,1,1,1,0) (5). These results indicate that the oxidation of hexapyrranes may be developed as an effective approach for the syntheses of novel linear and macrocyclic hexapyrroles.