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Diarylamine Synthesis via Desulfinylative Smiles Rearrangement

[Image: see text] Diarylamines are obtained directly from sulfinamides through a novel rearrangement sequence. The transformation is transition metal-free and proceeds under mild conditions, providing facile access to highly sterically hindered diarylamines that are otherwise inaccessible by traditi...

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Autores principales: Sephton, Thomas, Large, Jonathan M., Butterworth, Sam, Greaney, Michael F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8893360/
https://www.ncbi.nlm.nih.gov/pubmed/35094513
http://dx.doi.org/10.1021/acs.orglett.1c04122
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author Sephton, Thomas
Large, Jonathan M.
Butterworth, Sam
Greaney, Michael F.
author_facet Sephton, Thomas
Large, Jonathan M.
Butterworth, Sam
Greaney, Michael F.
author_sort Sephton, Thomas
collection PubMed
description [Image: see text] Diarylamines are obtained directly from sulfinamides through a novel rearrangement sequence. The transformation is transition metal-free and proceeds under mild conditions, providing facile access to highly sterically hindered diarylamines that are otherwise inaccessible by traditional S(N)Ar chemistry. The reaction highlights the distinct reactivity of the sulfinamide group in Smiles rearrangements versus that of the more common sulfonamides.
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spelling pubmed-88933602022-03-04 Diarylamine Synthesis via Desulfinylative Smiles Rearrangement Sephton, Thomas Large, Jonathan M. Butterworth, Sam Greaney, Michael F. Org Lett [Image: see text] Diarylamines are obtained directly from sulfinamides through a novel rearrangement sequence. The transformation is transition metal-free and proceeds under mild conditions, providing facile access to highly sterically hindered diarylamines that are otherwise inaccessible by traditional S(N)Ar chemistry. The reaction highlights the distinct reactivity of the sulfinamide group in Smiles rearrangements versus that of the more common sulfonamides. American Chemical Society 2022-01-30 2022-02-11 /pmc/articles/PMC8893360/ /pubmed/35094513 http://dx.doi.org/10.1021/acs.orglett.1c04122 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Sephton, Thomas
Large, Jonathan M.
Butterworth, Sam
Greaney, Michael F.
Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
title Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
title_full Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
title_fullStr Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
title_full_unstemmed Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
title_short Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
title_sort diarylamine synthesis via desulfinylative smiles rearrangement
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8893360/
https://www.ncbi.nlm.nih.gov/pubmed/35094513
http://dx.doi.org/10.1021/acs.orglett.1c04122
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