Accessing an azaborine building block: synthesis and substitution reactions of 2-chloromethyl-2,1-borazaronaphthalene.

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.