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Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(ii) diphosphite complexes
Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C–H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the prac...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6510317/ https://www.ncbi.nlm.nih.gov/pubmed/31160960 http://dx.doi.org/10.1039/c8sc05600e |
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author | Zhong, Jian-Ji To, Wai-Pong Liu, Yungen Lu, Wei Che, Chi-Ming |
author_facet | Zhong, Jian-Ji To, Wai-Pong Liu, Yungen Lu, Wei Che, Chi-Ming |
author_sort | Zhong, Jian-Ji |
collection | PubMed |
description | Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C–H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C–H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis. |
format | Online Article Text |
id | pubmed-6510317 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-65103172019-06-03 Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(ii) diphosphite complexes Zhong, Jian-Ji To, Wai-Pong Liu, Yungen Lu, Wei Che, Chi-Ming Chem Sci Chemistry Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C–H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C–H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis. Royal Society of Chemistry 2019-04-02 /pmc/articles/PMC6510317/ /pubmed/31160960 http://dx.doi.org/10.1039/c8sc05600e Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
spellingShingle | Chemistry Zhong, Jian-Ji To, Wai-Pong Liu, Yungen Lu, Wei Che, Chi-Ming Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(ii) diphosphite complexes |
title | Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(ii) diphosphite complexes
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title_full | Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(ii) diphosphite complexes
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title_fullStr | Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(ii) diphosphite complexes
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title_full_unstemmed | Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(ii) diphosphite complexes
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title_short | Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(ii) diphosphite complexes
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title_sort | efficient acceptorless photo-dehydrogenation of alcohols and n-heterocycles with binuclear platinum(ii) diphosphite complexes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6510317/ https://www.ncbi.nlm.nih.gov/pubmed/31160960 http://dx.doi.org/10.1039/c8sc05600e |
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