Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition‐metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce–Smiles rearrangemen...

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Detalles Bibliográficos
Autores principales: Holden, Catherine M., Sohel, Shariar M. A., Greaney, Michael F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4819888/
https://www.ncbi.nlm.nih.gov/pubmed/26762551
http://dx.doi.org/10.1002/anie.201510236
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author Holden, Catherine M.
Sohel, Shariar M. A.
Greaney, Michael F.
author_facet Holden, Catherine M.
Sohel, Shariar M. A.
Greaney, Michael F.
author_sort Holden, Catherine M.
collection PubMed
description A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition‐metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce–Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines.
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spelling pubmed-48198882016-04-28 Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce–Smiles Rearrangement Holden, Catherine M. Sohel, Shariar M. A. Greaney, Michael F. Angew Chem Int Ed Engl Communications A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition‐metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce–Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines. John Wiley and Sons Inc. 2016-01-13 2016-02 /pmc/articles/PMC4819888/ /pubmed/26762551 http://dx.doi.org/10.1002/anie.201510236 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Holden, Catherine M.
Sohel, Shariar M. A.
Greaney, Michael F.
Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce–Smiles Rearrangement
title Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce–Smiles Rearrangement
title_full Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce–Smiles Rearrangement
title_fullStr Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce–Smiles Rearrangement
title_full_unstemmed Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce–Smiles Rearrangement
title_short Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce–Smiles Rearrangement
title_sort metal free bi(hetero)aryl synthesis: a benzyne truce–smiles rearrangement
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4819888/
https://www.ncbi.nlm.nih.gov/pubmed/26762551
http://dx.doi.org/10.1002/anie.201510236
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AT greaneymichaelf metalfreebiheteroarylsynthesisabenzynetrucesmilesrearrangement

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