Metal-Free Functionalization of N,N-Dialkylanilines via Temporary Oxidation to N,N-Dialkylaniline N-Oxides and Group Transfer

[Image: see text] A simple set of protocols for the controlled elaboration of anilines is reported allowing access to a diverse array of aminophenols, aminoarylsulfonates, alkylated anilines, and aminoanilines in 29–95% yield in a single laboratory operation from easily isolable, bench-stable N,N-di...

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Autores principales: Lewis, Robert S., Wisthoff, Michael F., Grissmerson, J., Chain, William J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4105181/
https://www.ncbi.nlm.nih.gov/pubmed/24992642
http://dx.doi.org/10.1021/ol501813s
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author Lewis, Robert S.
Wisthoff, Michael F.
Grissmerson, J.
Chain, William J.
author_facet Lewis, Robert S.
Wisthoff, Michael F.
Grissmerson, J.
Chain, William J.
author_sort Lewis, Robert S.
collection PubMed
description [Image: see text] A simple set of protocols for the controlled elaboration of anilines is reported allowing access to a diverse array of aminophenols, aminoarylsulfonates, alkylated anilines, and aminoanilines in 29–95% yield in a single laboratory operation from easily isolable, bench-stable N,N-dialkylaniline N-oxides. The introduction of new C–O, C–C, and C–N bonds on the aromatic ring is made possible by a temporary increase in oxidation level and excision of a weak N–O bond.
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spelling pubmed-41051812015-07-03 Metal-Free Functionalization of N,N-Dialkylanilines via Temporary Oxidation to N,N-Dialkylaniline N-Oxides and Group Transfer Lewis, Robert S. Wisthoff, Michael F. Grissmerson, J. Chain, William J. Org Lett [Image: see text] A simple set of protocols for the controlled elaboration of anilines is reported allowing access to a diverse array of aminophenols, aminoarylsulfonates, alkylated anilines, and aminoanilines in 29–95% yield in a single laboratory operation from easily isolable, bench-stable N,N-dialkylaniline N-oxides. The introduction of new C–O, C–C, and C–N bonds on the aromatic ring is made possible by a temporary increase in oxidation level and excision of a weak N–O bond. American Chemical Society 2014-07-03 2014-07-18 /pmc/articles/PMC4105181/ /pubmed/24992642 http://dx.doi.org/10.1021/ol501813s Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Lewis, Robert S.
Wisthoff, Michael F.
Grissmerson, J.
Chain, William J.
Metal-Free Functionalization of N,N-Dialkylanilines via Temporary Oxidation to N,N-Dialkylaniline N-Oxides and Group Transfer
title Metal-Free Functionalization of N,N-Dialkylanilines via Temporary Oxidation to N,N-Dialkylaniline N-Oxides and Group Transfer
title_full Metal-Free Functionalization of N,N-Dialkylanilines via Temporary Oxidation to N,N-Dialkylaniline N-Oxides and Group Transfer
title_fullStr Metal-Free Functionalization of N,N-Dialkylanilines via Temporary Oxidation to N,N-Dialkylaniline N-Oxides and Group Transfer
title_full_unstemmed Metal-Free Functionalization of N,N-Dialkylanilines via Temporary Oxidation to N,N-Dialkylaniline N-Oxides and Group Transfer
title_short Metal-Free Functionalization of N,N-Dialkylanilines via Temporary Oxidation to N,N-Dialkylaniline N-Oxides and Group Transfer
title_sort metal-free functionalization of n,n-dialkylanilines via temporary oxidation to n,n-dialkylaniline n-oxides and group transfer
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4105181/
https://www.ncbi.nlm.nih.gov/pubmed/24992642
http://dx.doi.org/10.1021/ol501813s
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