Accessing 2-(Hetero)arylmethyl-, -allyl-, and -propargyl-2,1-borazaronaphthalenes: Palladium-Catalyzed Cross-Couplings of 2-(Chloromethyl)-2,1-borazaronaphthalenes

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• 作者：Gary A. Molander ; Javad Amani ; Steven R. Wisniewski
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：November 21, 2014
• 年：2014
• 卷：16
• 期：22
• 页码：6024-6027
• 全文大小：328K
• ISSN：1523-7052

文摘

The synthesis of 2-(chloromethyl)-2,1-borazaronaphthalene has provided an opportunity to expand dramatically the functionalization of the azaborines. This azaborinyl building block can serve as the electrophile in palladium-catalyzed cross-coupling reactions to form sp³鈥搒p and sp³鈥搒p² bonds. The cross-coupling reactions of 2-(chloromethyl)-2,1-borazaronaphthalene with potassium (hetero)aryl- and alkenyltrifluoroborates as well as terminal alkynes provides access to a variety of novel azaborines, allowing a library of pseudobenzylic substituted azaborines to be prepared from one common starting material.