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Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
A novel and straightforward strategy for functionalized 1H-indazoles is realized by the Rh(iii)-catalyzed double C–H activation and C–H/C–H cross coupling of readily available aldehyde phenylhydrazones. The reaction is scalable and various 1H-indazoles could be afforded in moderate to high yields wi...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5460599/ https://www.ncbi.nlm.nih.gov/pubmed/28616139 http://dx.doi.org/10.1039/c6sc03888c |
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author | Xu, Pan Wang, Guoqiang Wu, Zhongkai li, Shuhua Zhu, Chengjian |
author_facet | Xu, Pan Wang, Guoqiang Wu, Zhongkai li, Shuhua Zhu, Chengjian |
author_sort | Xu, Pan |
collection | PubMed |
description | A novel and straightforward strategy for functionalized 1H-indazoles is realized by the Rh(iii)-catalyzed double C–H activation and C–H/C–H cross coupling of readily available aldehyde phenylhydrazones. The reaction is scalable and various 1H-indazoles could be afforded in moderate to high yields with good functional-group compatibility. Mechanism experiments and DFT calculations suggest the distinctive Rh(iii)-catalyzed C–H/C–H cross coupling reaction underwent a cascade C(aryl)–H bond metalation, C(aldhyde)–H bond insertion and reductive elimination process. |
format | Online Article Text |
id | pubmed-5460599 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-54605992017-06-14 Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis Xu, Pan Wang, Guoqiang Wu, Zhongkai li, Shuhua Zhu, Chengjian Chem Sci Chemistry A novel and straightforward strategy for functionalized 1H-indazoles is realized by the Rh(iii)-catalyzed double C–H activation and C–H/C–H cross coupling of readily available aldehyde phenylhydrazones. The reaction is scalable and various 1H-indazoles could be afforded in moderate to high yields with good functional-group compatibility. Mechanism experiments and DFT calculations suggest the distinctive Rh(iii)-catalyzed C–H/C–H cross coupling reaction underwent a cascade C(aryl)–H bond metalation, C(aldhyde)–H bond insertion and reductive elimination process. Royal Society of Chemistry 2017-02-01 2016-10-07 /pmc/articles/PMC5460599/ /pubmed/28616139 http://dx.doi.org/10.1039/c6sc03888c Text en This journal is © The Royal Society of Chemistry 2016 https://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/ (https://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 Xu, Pan Wang, Guoqiang Wu, Zhongkai li, Shuhua Zhu, Chengjian Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis |
title | Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
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title_full | Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
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title_fullStr | Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
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title_full_unstemmed | Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
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title_short | Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
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title_sort | rh(iii)-catalyzed double c–h activation of aldehyde hydrazones: a route for functionalized 1h-indazole synthesis |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5460599/ https://www.ncbi.nlm.nih.gov/pubmed/28616139 http://dx.doi.org/10.1039/c6sc03888c |
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