Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp(3))–H functionalization

A new metal-free oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes is described. This reaction enables the formation of three new C–C bonds in a single reaction by a sequence of oxidative decarbonylation, radical additi...

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Autores principales: Li, Yang, Pan, Gao-Hui, Hu, Ming, Liu, Bang, Song, Ren-Jie, Li, Jin-Heng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5282743/
https://www.ncbi.nlm.nih.gov/pubmed/28337339
http://dx.doi.org/10.1039/c6sc02451c
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author Li, Yang
Pan, Gao-Hui
Hu, Ming
Liu, Bang
Song, Ren-Jie
Li, Jin-Heng
author_facet Li, Yang
Pan, Gao-Hui
Hu, Ming
Liu, Bang
Song, Ren-Jie
Li, Jin-Heng
author_sort Li, Yang
collection PubMed
description A new metal-free oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes is described. This reaction enables the formation of three new C–C bonds in a single reaction by a sequence of oxidative decarbonylation, radical addition across C–C unsaturated bonds, C–H functionalization and annulation, and represents the first oxidative decarbonylative [2 + 2 + 2] carbocyclization approach using tertiary and secondary alkyl aldehydes as a two carbon unit for assembling six-membered carbocycle-fused polycycles.
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spelling pubmed-52827432017-03-21 Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp(3))–H functionalization Li, Yang Pan, Gao-Hui Hu, Ming Liu, Bang Song, Ren-Jie Li, Jin-Heng Chem Sci Chemistry A new metal-free oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes is described. This reaction enables the formation of three new C–C bonds in a single reaction by a sequence of oxidative decarbonylation, radical addition across C–C unsaturated bonds, C–H functionalization and annulation, and represents the first oxidative decarbonylative [2 + 2 + 2] carbocyclization approach using tertiary and secondary alkyl aldehydes as a two carbon unit for assembling six-membered carbocycle-fused polycycles. Royal Society of Chemistry 2016-12-01 2016-07-21 /pmc/articles/PMC5282743/ /pubmed/28337339 http://dx.doi.org/10.1039/c6sc02451c Text en This journal is © The Royal Society of Chemistry 2016 http://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/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Li, Yang
Pan, Gao-Hui
Hu, Ming
Liu, Bang
Song, Ren-Jie
Li, Jin-Heng
Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp(3))–H functionalization
title Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp(3))–H functionalization
title_full Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp(3))–H functionalization
title_fullStr Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp(3))–H functionalization
title_full_unstemmed Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp(3))–H functionalization
title_short Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp(3))–H functionalization
title_sort intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of n-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving c(sp(3))–h functionalization
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5282743/
https://www.ncbi.nlm.nih.gov/pubmed/28337339
http://dx.doi.org/10.1039/c6sc02451c
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