Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
Authors:
Open Access
- 15 October 2014
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 16 (21) , 5636-5639
Abstract
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.Keywords
Funding Information
- National Institute of General Medical Sciences (R01 GM-081376)
- Eli Lilly and Company
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