Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation

A titanocene‐catalyzed regiodivergent radical arylation is described that allows access to either enantiomerically pure tetrahydroquinolines or indolines from a common starting material. The regioselectivity of epoxide opening that results in the high selectivity of heterocycle formation is controll...

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Autores principales: Mühlhaus, Felix, Weißbarth, Hendrik, Dahmen, Tobias, Schnakenburg, Gregor, Gansäuer, Andreas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6852184/
https://www.ncbi.nlm.nih.gov/pubmed/31394024
http://dx.doi.org/10.1002/anie.201908860
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author Mühlhaus, Felix
Weißbarth, Hendrik
Dahmen, Tobias
Schnakenburg, Gregor
Gansäuer, Andreas
author_facet Mühlhaus, Felix
Weißbarth, Hendrik
Dahmen, Tobias
Schnakenburg, Gregor
Gansäuer, Andreas
author_sort Mühlhaus, Felix
collection PubMed
description A titanocene‐catalyzed regiodivergent radical arylation is described that allows access to either enantiomerically pure tetrahydroquinolines or indolines from a common starting material. The regioselectivity of epoxide opening that results in the high selectivity of heterocycle formation is controlled by two factors, the absolute configuration of the enantiopure ligands of the (C(5)H(4)R)(2)TiX(2) catalyst and the inorganic ligand X (X=Cl, OTs). The overall reaction is atom‐economical and constitutes a radical Friedel–Crafts alkylation.
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spelling pubmed-68521842019-11-22 Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation Mühlhaus, Felix Weißbarth, Hendrik Dahmen, Tobias Schnakenburg, Gregor Gansäuer, Andreas Angew Chem Int Ed Engl Communications A titanocene‐catalyzed regiodivergent radical arylation is described that allows access to either enantiomerically pure tetrahydroquinolines or indolines from a common starting material. The regioselectivity of epoxide opening that results in the high selectivity of heterocycle formation is controlled by two factors, the absolute configuration of the enantiopure ligands of the (C(5)H(4)R)(2)TiX(2) catalyst and the inorganic ligand X (X=Cl, OTs). The overall reaction is atom‐economical and constitutes a radical Friedel–Crafts alkylation. John Wiley and Sons Inc. 2019-08-28 2019-10-01 /pmc/articles/PMC6852184/ /pubmed/31394024 http://dx.doi.org/10.1002/anie.201908860 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the 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
Mühlhaus, Felix
Weißbarth, Hendrik
Dahmen, Tobias
Schnakenburg, Gregor
Gansäuer, Andreas
Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation
title Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation
title_full Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation
title_fullStr Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation
title_full_unstemmed Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation
title_short Merging Regiodivergent Catalysis with Atom‐Economical Radical Arylation
title_sort merging regiodivergent catalysis with atom‐economical radical arylation
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6852184/
https://www.ncbi.nlm.nih.gov/pubmed/31394024
http://dx.doi.org/10.1002/anie.201908860
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AT schnakenburggregor mergingregiodivergentcatalysiswithatomeconomicalradicalarylation
AT gansauerandreas mergingregiodivergentcatalysiswithatomeconomicalradicalarylation

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