Accessing an azaborine building block: synthesis and substitution reactions of 2-chloromethyl-2,1-borazaronaphthalene.
Accessing an azaborine building block: synthesis and substitution reactions of 2-chloromethyl-2,1-borazaronaphthalene.
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DOI：
10.1021/ol502708z
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发表时间：
2014-11-07
期刊：
影响因子：
5.2
通讯作者：
Amani J
中科院分区：
文献类型：
--
作者：
Molander GA;Wisniewski SR;Amani J
合成苄胺、醚和酯的一种主要合成路线是苄基卤化物的亲核取代。为了开发一种用于等排氮杂硼烷的简便合成和官能化的方法，一步合成了2-氯甲基-2,1-硼扎萘，以提供类似的苄基卤化物的常见前体。这种 B-N 电子等排体已被证明是一种有效的构建模块，可在多种亲核试剂的取代反应中充当亲电子试剂。
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–N isostere has been shown to be an effective building block by serving as an electrophile in substitution reactions with a large variety of nucleophiles.