Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides

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• 作者：George Blessley ; Patrick Holden ; Matthew Walker ; John M. Brown ; V茅ronique Gouverneur
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：June 1, 2012
• 年：2012
• 卷：14
• 期：11
• 页码：2754-2757
• 全文大小：293K
• 年卷期：v.14,no.11(June 1, 2012)
• ISSN：1523-7052

文摘

Benzylic fluorides are suitable substrates for Pd(0)-catalyzed Tsuji鈥揟rost substitution using carbon, nitrogen, oxygen, and sulfur nucleophiles and for cross-coupling with phenylboronic acid. For the bifunctional substrate 4-chlorobenzyl fluoride, fine-tuning of the reaction conditions allows for the regioselective displacement of either the chlorine or fluorine substituent. The leaving group ability of fluoride vs other groups displaced in substitution is CF₃CO₂ 鈮?p-NO₂C₆H₄CO₂ 鈮?OCO₂CH₃ > F > CH₃CO₂, a ranking similar to allylic fluorides under Pd catalysis.