Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene

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• 作者：Gary A. Molander ; Steven R. Wisniewski ; Javad Amani
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：November 7, 2014
• 年：2014
• 卷：16
• 期：21
• 页码：5636-5639
• 全文大小：354K
• ISSN：1523-7052

文摘

One major synthetic route to the synthesis of benzyl amines, ethers, and esters is the nucleophilic substitution of a benzylic halide. To develop a method for the facile synthesis and functionalization of the isosteric azaborines, 2-chloromethyl-2,1-borazaronaphthalene has been synthesized in one step to afford a similar common precursor to a benzylic halide. This B鈥揘 isostere has been shown to be an effective building block by serving as an electrophile in substitution reactions with a large variety of nucleophiles.