Friedel–Crafts acylation of ferrocene with alkynoic acids

详细信息    查看全文

• 作者：Damian Plaż ; uk ; J. Zakrzewski
• 关键词：Ferrocene ; Friedel– ; Crafts acylation ; Alkynoic acid ; Ynone ; “ ; Click” ; chemistry
• 刊名：Journal of Organometallic Chemistry
• 出版年：2009
• 出版时间：15 May 2009
• 年：2009
• 卷：694
• 期：12
• 页码：1802-1806
• 全文大小：317 K

文摘

Ferrocene reacts with alkynoic acids (conjugated or nonconjugated terminal), trifluoroacetic anhydride and triflic acid (or boron trifluoride etherate) to afford the corresponding ferrocenyl ynones in good yields. Only in the case of propynoic- and 3-butynoic acid complex, untreatable reaction mixtures were obtained. However, propynoilferrocene was obtained by desilylation of (trimethylsilyl)propynoilferrocene with KF/18-crown-6. Reaction with nonconjugated terminal alkynoic acids, carried out in the presence of a large excess of triflic acid (4 equiv.) results in formation of complex mixtures of products (in the reaction with 4-pentynoic acid enol triflate of ferrocenyl 1,4-diketone and 2-ferrocenyl-5-methylfuran were isolated). Ferrocenyl ynones obtained in this work can be used for synthesis of more complex ferrocenyl systems by “click” chemistry.