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Synthetic Approaches for C-N Bonds by TiO(2) Photocatalysis

Nitrogen-containing organic compounds possess the most important status in drug molecules and agricultural chemicals. More than 80% currently used drugs have at least a C-N bond. The green and mild methodology to prepare diverse C-N bonds to replace traditional harsh preparation protocols is always...

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Autores principales: Ma, Dongge, Zhai, Shan, Wang, Yi, Liu, Anan, Chen, Chuncheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6759479/
https://www.ncbi.nlm.nih.gov/pubmed/31620428
http://dx.doi.org/10.3389/fchem.2019.00635
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author Ma, Dongge
Zhai, Shan
Wang, Yi
Liu, Anan
Chen, Chuncheng
author_facet Ma, Dongge
Zhai, Shan
Wang, Yi
Liu, Anan
Chen, Chuncheng
author_sort Ma, Dongge
collection PubMed
description Nitrogen-containing organic compounds possess the most important status in drug molecules and agricultural chemicals. More than 80% currently used drugs have at least a C-N bond. The green and mild methodology to prepare diverse C-N bonds to replace traditional harsh preparation protocols is always a hotspot in modern synthetic chemistry. TiO(2)-based nanomaterials, considered as environmentally benign, stable, and powerful photocatalysts, have recently been applied in some certain challenging organic synthesis including construction of useful C-N compounds under mild conditions that are impossible to complete by conventional catalysis. This mini review would present state-of-the-art paragon examples of TiO(2) photocatalyzed C-N bond formations. The discussion would be divided into two main sections: (1) N-alkylation of amines and (2) C-N formation in heterocycle synthesis. Especially, the mechanism of TiO(2) photocatalytic C-N bond formation through activating alcohol into C=O by photo-induced hole followed by C=NH-R formation and finally hydrogenating C=NH-R into C-N bonds by combination of photo-induced electron/H(+) assisted with loaded-Pt would be covered in detail. We believe that the mini-review will bring new insights into TiO(2) photocatalysis applied to construct challenging organic compounds through enabling photo-induced hole and electron in a concerted way on coupling two substrate molecules together with respect to their conventionally independent catalysis behavior.
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spelling pubmed-67594792019-10-16 Synthetic Approaches for C-N Bonds by TiO(2) Photocatalysis Ma, Dongge Zhai, Shan Wang, Yi Liu, Anan Chen, Chuncheng Front Chem Chemistry Nitrogen-containing organic compounds possess the most important status in drug molecules and agricultural chemicals. More than 80% currently used drugs have at least a C-N bond. The green and mild methodology to prepare diverse C-N bonds to replace traditional harsh preparation protocols is always a hotspot in modern synthetic chemistry. TiO(2)-based nanomaterials, considered as environmentally benign, stable, and powerful photocatalysts, have recently been applied in some certain challenging organic synthesis including construction of useful C-N compounds under mild conditions that are impossible to complete by conventional catalysis. This mini review would present state-of-the-art paragon examples of TiO(2) photocatalyzed C-N bond formations. The discussion would be divided into two main sections: (1) N-alkylation of amines and (2) C-N formation in heterocycle synthesis. Especially, the mechanism of TiO(2) photocatalytic C-N bond formation through activating alcohol into C=O by photo-induced hole followed by C=NH-R formation and finally hydrogenating C=NH-R into C-N bonds by combination of photo-induced electron/H(+) assisted with loaded-Pt would be covered in detail. We believe that the mini-review will bring new insights into TiO(2) photocatalysis applied to construct challenging organic compounds through enabling photo-induced hole and electron in a concerted way on coupling two substrate molecules together with respect to their conventionally independent catalysis behavior. Frontiers Media S.A. 2019-09-18 /pmc/articles/PMC6759479/ /pubmed/31620428 http://dx.doi.org/10.3389/fchem.2019.00635 Text en Copyright © 2019 Ma, Zhai, Wang, Liu and Chen. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Ma, Dongge
Zhai, Shan
Wang, Yi
Liu, Anan
Chen, Chuncheng
Synthetic Approaches for C-N Bonds by TiO(2) Photocatalysis
title Synthetic Approaches for C-N Bonds by TiO(2) Photocatalysis
title_full Synthetic Approaches for C-N Bonds by TiO(2) Photocatalysis
title_fullStr Synthetic Approaches for C-N Bonds by TiO(2) Photocatalysis
title_full_unstemmed Synthetic Approaches for C-N Bonds by TiO(2) Photocatalysis
title_short Synthetic Approaches for C-N Bonds by TiO(2) Photocatalysis
title_sort synthetic approaches for c-n bonds by tio(2) photocatalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6759479/
https://www.ncbi.nlm.nih.gov/pubmed/31620428
http://dx.doi.org/10.3389/fchem.2019.00635
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