Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(iii) precatalyst bearing sterically bulky substituents. While the prototypical Cp* ligand provides product with low selectivity, sterically bulky Cp(t) affords p...

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Detalles Bibliográficos
Autores principales: Hyster, Todd K., Dalton, Derek M., Rovis, Tomislav
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4256080/
https://www.ncbi.nlm.nih.gov/pubmed/25489470
http://dx.doi.org/10.1039/c4sc02590c
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author Hyster, Todd K.
Dalton, Derek M.
Rovis, Tomislav
author_facet Hyster, Todd K.
Dalton, Derek M.
Rovis, Tomislav
author_sort Hyster, Todd K.
collection PubMed
description We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(iii) precatalyst bearing sterically bulky substituents. While the prototypical Cp* ligand provides product with low selectivity, sterically bulky Cp(t) affords product with excellent regioselectivity for a range of benzhydroxamic acids and alkenes. Crystallographic evidence offers insight as to the source of the increased regioselectivity.
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spelling pubmed-42560802016-01-01 Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones Hyster, Todd K. Dalton, Derek M. Rovis, Tomislav Chem Sci Chemistry We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(iii) precatalyst bearing sterically bulky substituents. While the prototypical Cp* ligand provides product with low selectivity, sterically bulky Cp(t) affords product with excellent regioselectivity for a range of benzhydroxamic acids and alkenes. Crystallographic evidence offers insight as to the source of the increased regioselectivity. Royal Society of Chemistry 2015-01-01 2014-10-01 /pmc/articles/PMC4256080/ /pubmed/25489470 http://dx.doi.org/10.1039/c4sc02590c Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Hyster, Todd K.
Dalton, Derek M.
Rovis, Tomislav
Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
title Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
title_full Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
title_fullStr Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
title_full_unstemmed Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
title_short Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
title_sort ligand design for rh(iii)-catalyzed c–h activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4256080/
https://www.ncbi.nlm.nih.gov/pubmed/25489470
http://dx.doi.org/10.1039/c4sc02590c
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AT rovistomislav liganddesignforrhiiicatalyzedchactivationanunsymmetricalcyclopentadienylgroupenablesaregioselectivesynthesisofdihydroisoquinolones

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