Regioselective, Directed Meta Acylation of Aromatic Compounds

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• 作者：Shuji Akai ; Andrew J. Peat ; and Stephen L. Buchwald
• 刊名：Journal of the American Chemical Society
• 出版年：1998
• 出版时间：September 16, 1998
• 年：1998
• 卷：120
• 期：36
• 页码：9119 - 9125
• 全文大小：188K
• 年卷期：v.120,no.36(September 16, 1998)
• ISSN：1520-5126

文摘

A new method for the directed meta acylation of aromatic compounds is described. This methodinvolves an ortho lithiation procedure combined with zirconocene-benzyne chemistry. 3-Acyl-1-substitutedbenzene derivatives were obtained by acidic hydrolysis of the azazirconacycle intermediate which results fromthe coupling of a nitrile with a zirconocene-benzyne complex. Similarly, 3-acyl-2-iodo-1-substituted benzenederivatives were obtained by the iodination of the same intermediate followed by acidic hydrolysis. Theseprocedures, which utilize simple, readily available starting materials, give good yields of regiochemically pureproducts.