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A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions

A chiral phosphoric acid with a 2,2’‐binaphthol core was prepared that displays two thioxanthone moieties at the 3,3’‐position as light‐harvesting antennas. Despite its relatively low triplet energy, the phosphoric acid was found to be an efficient catalyst for the enantioselective intermolecular [2...

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Autores principales: Pecho, Franziska, Zou, You‐Quan, Gramüller, Johannes, Mori, Tadashi, Huber, Stefan M., Bauer, Andreas, Gschwind, Ruth M., Bach, Thorsten
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7216904/
https://www.ncbi.nlm.nih.gov/pubmed/32065432
http://dx.doi.org/10.1002/chem.202000720
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author Pecho, Franziska
Zou, You‐Quan
Gramüller, Johannes
Mori, Tadashi
Huber, Stefan M.
Bauer, Andreas
Gschwind, Ruth M.
Bach, Thorsten
author_facet Pecho, Franziska
Zou, You‐Quan
Gramüller, Johannes
Mori, Tadashi
Huber, Stefan M.
Bauer, Andreas
Gschwind, Ruth M.
Bach, Thorsten
author_sort Pecho, Franziska
collection PubMed
description A chiral phosphoric acid with a 2,2’‐binaphthol core was prepared that displays two thioxanthone moieties at the 3,3’‐position as light‐harvesting antennas. Despite its relatively low triplet energy, the phosphoric acid was found to be an efficient catalyst for the enantioselective intermolecular [2+2] photocycloaddition of β‐carboxyl‐substituted cyclic enones (e.r. up to 93:7). Binding of the carboxylic acid to the sensitizer is suggested by NMR studies and by DFT calculations to occur by means of two hydrogen bonds. The binding event not only enables an enantioface differentiation but also modulates the triplet energy of the substrates.
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spelling pubmed-72169042020-05-13 A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions Pecho, Franziska Zou, You‐Quan Gramüller, Johannes Mori, Tadashi Huber, Stefan M. Bauer, Andreas Gschwind, Ruth M. Bach, Thorsten Chemistry Communications A chiral phosphoric acid with a 2,2’‐binaphthol core was prepared that displays two thioxanthone moieties at the 3,3’‐position as light‐harvesting antennas. Despite its relatively low triplet energy, the phosphoric acid was found to be an efficient catalyst for the enantioselective intermolecular [2+2] photocycloaddition of β‐carboxyl‐substituted cyclic enones (e.r. up to 93:7). Binding of the carboxylic acid to the sensitizer is suggested by NMR studies and by DFT calculations to occur by means of two hydrogen bonds. The binding event not only enables an enantioface differentiation but also modulates the triplet energy of the substrates. John Wiley and Sons Inc. 2020-04-15 2020-04-21 /pmc/articles/PMC7216904/ /pubmed/32065432 http://dx.doi.org/10.1002/chem.202000720 Text en © 2020 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-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Pecho, Franziska
Zou, You‐Quan
Gramüller, Johannes
Mori, Tadashi
Huber, Stefan M.
Bauer, Andreas
Gschwind, Ruth M.
Bach, Thorsten
A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions
title A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions
title_full A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions
title_fullStr A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions
title_full_unstemmed A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions
title_short A Thioxanthone Sensitizer with a Chiral Phosphoric Acid Binding Site: Properties and Applications in Visible Light‐Mediated Cycloadditions
title_sort thioxanthone sensitizer with a chiral phosphoric acid binding site: properties and applications in visible light‐mediated cycloadditions
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7216904/
https://www.ncbi.nlm.nih.gov/pubmed/32065432
http://dx.doi.org/10.1002/chem.202000720
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