Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones

Dodecahydrotriphenylene, a higher homologue of trindane chemoselectively undergoes unidirectional benzylic sp(3) C–H oxidation and the central benzene ring remains intact unlike that in trindane under similar reaction conditions. RuO(4) which generally attacks sp(2) C–H to form oxidative products is...

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Autores principales: Bhatt, Gaurang J., Deota, Pradeep T., Upadhyay, Deepak, Jha, Prafulla K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9042685/
https://www.ncbi.nlm.nih.gov/pubmed/35494771
http://dx.doi.org/10.1039/d1ra06897k
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author Bhatt, Gaurang J.
Deota, Pradeep T.
Upadhyay, Deepak
Jha, Prafulla K.
author_facet Bhatt, Gaurang J.
Deota, Pradeep T.
Upadhyay, Deepak
Jha, Prafulla K.
author_sort Bhatt, Gaurang J.
collection PubMed
description Dodecahydrotriphenylene, a higher homologue of trindane chemoselectively undergoes unidirectional benzylic sp(3) C–H oxidation and the central benzene ring remains intact unlike that in trindane under similar reaction conditions. RuO(4) which generally attacks sp(2) C–H to form oxidative products is found to give benzylic ketones via sp(3) C–H oxidation. Density functional theory (DFT) calculations have also been performed to analyse the potential energy, energy barrier and HOMO–LUMO energy gap of the products.
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spelling pubmed-90426852022-04-28 Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones Bhatt, Gaurang J. Deota, Pradeep T. Upadhyay, Deepak Jha, Prafulla K. RSC Adv Chemistry Dodecahydrotriphenylene, a higher homologue of trindane chemoselectively undergoes unidirectional benzylic sp(3) C–H oxidation and the central benzene ring remains intact unlike that in trindane under similar reaction conditions. RuO(4) which generally attacks sp(2) C–H to form oxidative products is found to give benzylic ketones via sp(3) C–H oxidation. Density functional theory (DFT) calculations have also been performed to analyse the potential energy, energy barrier and HOMO–LUMO energy gap of the products. The Royal Society of Chemistry 2021-10-20 /pmc/articles/PMC9042685/ /pubmed/35494771 http://dx.doi.org/10.1039/d1ra06897k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Bhatt, Gaurang J.
Deota, Pradeep T.
Upadhyay, Deepak
Jha, Prafulla K.
Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones
title Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones
title_full Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones
title_fullStr Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones
title_full_unstemmed Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones
title_short Site-selective unidirectional benzylic sp(3) C–H oxidation of dodecahydrotriphenylene with RuCl(3)–NaIO(4): formation of benzylic ketones
title_sort site-selective unidirectional benzylic sp(3) c–h oxidation of dodecahydrotriphenylene with rucl(3)–naio(4): formation of benzylic ketones
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9042685/
https://www.ncbi.nlm.nih.gov/pubmed/35494771
http://dx.doi.org/10.1039/d1ra06897k
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