Metal-free tandem carbene N–H insertions and C–C bond cleavages

A metal-free C–H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. Compared to the simple N–H insertion manipulation of diazo, this method elegantly accomplishes a tandem N–H...

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Detalles Bibliográficos
Autores principales: Chen, Pu, Nan, Jiang, Hu, Yan, Kang, Yifan, Wang, Bo, Ma, Yangmin, Szostak, Michal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8178978/
https://www.ncbi.nlm.nih.gov/pubmed/34163814
http://dx.doi.org/10.1039/d0sc05763k
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author Chen, Pu
Nan, Jiang
Hu, Yan
Kang, Yifan
Wang, Bo
Ma, Yangmin
Szostak, Michal
author_facet Chen, Pu
Nan, Jiang
Hu, Yan
Kang, Yifan
Wang, Bo
Ma, Yangmin
Szostak, Michal
author_sort Chen, Pu
collection PubMed
description A metal-free C–H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. Compared to the simple N–H insertion manipulation of diazo, this method elegantly accomplishes a tandem N–H insertion/S(E)Ar/C–C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids.
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spelling pubmed-81789782021-06-22 Metal-free tandem carbene N–H insertions and C–C bond cleavages Chen, Pu Nan, Jiang Hu, Yan Kang, Yifan Wang, Bo Ma, Yangmin Szostak, Michal Chem Sci Chemistry A metal-free C–H [5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. Compared to the simple N–H insertion manipulation of diazo, this method elegantly accomplishes a tandem N–H insertion/S(E)Ar/C–C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids. The Royal Society of Chemistry 2020-11-10 /pmc/articles/PMC8178978/ /pubmed/34163814 http://dx.doi.org/10.1039/d0sc05763k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chen, Pu
Nan, Jiang
Hu, Yan
Kang, Yifan
Wang, Bo
Ma, Yangmin
Szostak, Michal
Metal-free tandem carbene N–H insertions and C–C bond cleavages
title Metal-free tandem carbene N–H insertions and C–C bond cleavages
title_full Metal-free tandem carbene N–H insertions and C–C bond cleavages
title_fullStr Metal-free tandem carbene N–H insertions and C–C bond cleavages
title_full_unstemmed Metal-free tandem carbene N–H insertions and C–C bond cleavages
title_short Metal-free tandem carbene N–H insertions and C–C bond cleavages
title_sort metal-free tandem carbene n–h insertions and c–c bond cleavages
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8178978/
https://www.ncbi.nlm.nih.gov/pubmed/34163814
http://dx.doi.org/10.1039/d0sc05763k
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