Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines

[Image: see text] An enantiospecific coupling between alkylboronic esters and lithiated aryl hydrazines is described. The reaction proceeds under transition-metal-free conditions and is promoted by acylation of a hydrazinyl arylboronate complex, which triggers a N–N bond cleavage with concomitant 1,...

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Autores principales: Ganesh, Venkataraman, Noble, Adam, Aggarwal, Varinder K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6178205/
https://www.ncbi.nlm.nih.gov/pubmed/30221524
http://dx.doi.org/10.1021/acs.orglett.8b02615
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author Ganesh, Venkataraman
Noble, Adam
Aggarwal, Varinder K.
author_facet Ganesh, Venkataraman
Noble, Adam
Aggarwal, Varinder K.
author_sort Ganesh, Venkataraman
collection PubMed
description [Image: see text] An enantiospecific coupling between alkylboronic esters and lithiated aryl hydrazines is described. The reaction proceeds under transition-metal-free conditions and is promoted by acylation of a hydrazinyl arylboronate complex, which triggers a N–N bond cleavage with concomitant 1,2-metalate rearrangement. Judicious choice of the acylating agent enabled the synthesis of ortho- and para-substituted anilines with essentially complete enantiospecificity from a wide range of boronic ester substrates.
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spelling pubmed-61782052018-10-11 Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines Ganesh, Venkataraman Noble, Adam Aggarwal, Varinder K. Org Lett [Image: see text] An enantiospecific coupling between alkylboronic esters and lithiated aryl hydrazines is described. The reaction proceeds under transition-metal-free conditions and is promoted by acylation of a hydrazinyl arylboronate complex, which triggers a N–N bond cleavage with concomitant 1,2-metalate rearrangement. Judicious choice of the acylating agent enabled the synthesis of ortho- and para-substituted anilines with essentially complete enantiospecificity from a wide range of boronic ester substrates. American Chemical Society 2018-09-17 2018-10-05 /pmc/articles/PMC6178205/ /pubmed/30221524 http://dx.doi.org/10.1021/acs.orglett.8b02615 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Ganesh, Venkataraman
Noble, Adam
Aggarwal, Varinder K.
Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines
title Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines
title_full Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines
title_fullStr Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines
title_full_unstemmed Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines
title_short Chiral Aniline Synthesis via Stereospecific C(sp(3))–C(sp(2)) Coupling of Boronic Esters with Aryl Hydrazines
title_sort chiral aniline synthesis via stereospecific c(sp(3))–c(sp(2)) coupling of boronic esters with aryl hydrazines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6178205/
https://www.ncbi.nlm.nih.gov/pubmed/30221524
http://dx.doi.org/10.1021/acs.orglett.8b02615
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AT aggarwalvarinderk chiralanilinesynthesisviastereospecificcsp3csp2couplingofboronicesterswitharylhydrazines

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