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Issue 12, 2016
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Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp3)–H functionalization

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Abstract

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.

Graphical abstract: Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp3)–H functionalization

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Publication details

The article was received on 03 Jun 2016, accepted on 16 Jul 2016 and first published on 21 Jul 2016


Article type: Edge Article
DOI: 10.1039/C6SC02451C
Citation: Chem. Sci., 2016,7, 7050-7054
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    Intermolecular oxidative decarbonylative [2 + 2 + 2] carbocyclization of N-(2-ethynylaryl)acrylamides with tertiary and secondary alkyl aldehydes involving C(sp3)–H functionalization

    Y. Li, G. Pan, M. Hu, B. Liu, R. Song and J. Li, Chem. Sci., 2016, 7, 7050
    DOI: 10.1039/C6SC02451C

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