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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...

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Autores principales: Xu, Pan, Wang, Guoqiang, Wu, Zhongkai, li, Shuhua, Zhu, Chengjian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
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.
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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
title_full Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
title_fullStr Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
title_full_unstemmed Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
title_short Rh(iii)-catalyzed double C–H activation of aldehyde hydrazones: a route for functionalized 1H-indazole synthesis
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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