Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes

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• 作者：Janina Bucher ; Thomas Wurm ; Svenja Taschinski ; Eleni Sachs ; David Ascough ; Matthias Rudolph ; Frank Rominger and A. Stephen K. Hashmi
• 刊名：Advanced Synthesis & Catalysis
• 出版年：2017
• 出版时间：January 19, 2017
• 年：2017
• 卷：359
• 期：2
• 页码：225-233
• 全文大小：988K
• ISSN：1615-4169

文摘

1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp²)–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield.