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

[Image: see text] 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 syn...

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Autores principales: Molander, Gary A., Wisniewski, Steven R., Amani, Javad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4227543/
https://www.ncbi.nlm.nih.gov/pubmed/25317850
http://dx.doi.org/10.1021/ol502708z
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author Molander, Gary A.
Wisniewski, Steven R.
Amani, Javad
author_facet Molander, Gary A.
Wisniewski, Steven R.
Amani, Javad
author_sort Molander, Gary A.
collection PubMed
description [Image: see text] 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.
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spelling pubmed-42275432015-10-15 Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene Molander, Gary A. Wisniewski, Steven R. Amani, Javad Org Lett [Image: see text] 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. American Chemical Society 2014-10-15 2014-11-07 /pmc/articles/PMC4227543/ /pubmed/25317850 http://dx.doi.org/10.1021/ol502708z Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Molander, Gary A.
Wisniewski, Steven R.
Amani, Javad
Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
title Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
title_full Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
title_fullStr Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
title_full_unstemmed Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
title_short Accessing an Azaborine Building Block: Synthesis and Substitution Reactions of 2-Chloromethyl-2,1-borazaronaphthalene
title_sort accessing an azaborine building block: synthesis and substitution reactions of 2-chloromethyl-2,1-borazaronaphthalene
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4227543/
https://www.ncbi.nlm.nih.gov/pubmed/25317850
http://dx.doi.org/10.1021/ol502708z
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