Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp3)鈥揌 Bonds

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• 作者：Jinmin Miao ; Ke Yang ; Martin Kurek ; Haibo Ge
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：August 7, 2015
• 年：2015
• 卷：17
• 期：15
• 页码：3738-3741
• 全文大小：459K
• ISSN：1523-7052

文摘

The transition-metal-catalyzed direct C鈥揌 bond fluorination is an attractive synthetic tool toward the preparation of organofluorines. While many methods exist for the direct sp³ C鈥揌 functionalization, site-selective fluorination of unactivated sp³ carbons remains a challenge. Direct, highly site-selective and diastereoselective fluorination of aliphatic amides via a palladium-catalyzed bidentate ligand-directed C鈥揌 bond functionalization process on unactivated sp³ carbons is reported. With this approach, a wide variety of 尾-fluorinated amino acid derivatives and aliphatic amides, important motifs in medicinal and agricultural chemistry, were prepared with palladium acetate as the catalyst and Selectfluor as the fluorine source.