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Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines
We describe an iron‐catalyzed asymmetric oxidative C−C coupling of diarylamines which proceeds at room temperature with air as final oxidant. Using hexadecafluorophthalocyanine‐iron(II) as catalyst in the presence of catalytic amounts of an axially chiral biaryl phosphoric acid, the resulting chiral...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10100243/ https://www.ncbi.nlm.nih.gov/pubmed/36269611 http://dx.doi.org/10.1002/chem.202203269 |
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author | Fritsche, Raphael F. Schuh, Tristan Kataeva, Olga Knölker, Hans‐Joachim |
author_facet | Fritsche, Raphael F. Schuh, Tristan Kataeva, Olga Knölker, Hans‐Joachim |
author_sort | Fritsche, Raphael F. |
collection | PubMed |
description | We describe an iron‐catalyzed asymmetric oxidative C−C coupling of diarylamines which proceeds at room temperature with air as final oxidant. Using hexadecafluorophthalocyanine‐iron(II) as catalyst in the presence of catalytic amounts of an axially chiral biaryl phosphoric acid, the resulting chiral 2,2′‐diamino‐1,1′‐biaryls are obtained in up to 90 % ee as confirmed by chiral HPLC. A detailed mechanism has been proposed with a radical cation‐chiral phosphate ion pair as key intermediate leading to the observed asymmetric induction. |
format | Online Article Text |
id | pubmed-10100243 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-101002432023-04-14 Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines Fritsche, Raphael F. Schuh, Tristan Kataeva, Olga Knölker, Hans‐Joachim Chemistry Research Articles We describe an iron‐catalyzed asymmetric oxidative C−C coupling of diarylamines which proceeds at room temperature with air as final oxidant. Using hexadecafluorophthalocyanine‐iron(II) as catalyst in the presence of catalytic amounts of an axially chiral biaryl phosphoric acid, the resulting chiral 2,2′‐diamino‐1,1′‐biaryls are obtained in up to 90 % ee as confirmed by chiral HPLC. A detailed mechanism has been proposed with a radical cation‐chiral phosphate ion pair as key intermediate leading to the observed asymmetric induction. John Wiley and Sons Inc. 2022-11-27 2023-01-27 /pmc/articles/PMC10100243/ /pubmed/36269611 http://dx.doi.org/10.1002/chem.202203269 Text en © 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ (https://creativecommons.org/licenses/by-nc-nd/4.0/) License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Research Articles Fritsche, Raphael F. Schuh, Tristan Kataeva, Olga Knölker, Hans‐Joachim Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines |
title | Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines
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title_full | Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines
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title_fullStr | Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines
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title_full_unstemmed | Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines
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title_short | Atroposelective Synthesis of 2,2′‐Bis(arylamino)‐1,1′‐biaryls by Oxidative Iron(III)‐ and Phosphoric Acid‐Catalyzed C−C Coupling of Diarylamines
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title_sort | atroposelective synthesis of 2,2′‐bis(arylamino)‐1,1′‐biaryls by oxidative iron(iii)‐ and phosphoric acid‐catalyzed c−c coupling of diarylamines |
topic | Research Articles |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10100243/ https://www.ncbi.nlm.nih.gov/pubmed/36269611 http://dx.doi.org/10.1002/chem.202203269 |
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