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Regio- and stereo-selective decarbonylative alkylative arylation of terminal alkynes with aliphatic aldehydes and arenes via dual C–H bond functionalization

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Abstract

A convenient Cu-promoted three-component decarbonylative alkylative arylation of terminal alkynes with aliphatic aldehydes and arenes is developed to provide chain elongated tri-substituted olefins with good chemo-, regio- and stereo-selectivities, and is applied to the radical-type decarbonylative coupling of sugar analogs. Readily available aliphatic aldehydes are readily decarbonylated into 1˙, 2˙ and 3˙ alkyl radicals for the construction of a C(sp3)–C(sp2) bond via radical addition, followed by HAS-arylation to form the C(sp2)–C(sp2) bond.

Graphical abstract: Regio- and stereo-selective decarbonylative alkylative arylation of terminal alkynes with aliphatic aldehydes and arenes via dual C–H bond functionalization

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Publication details

The article was received on 13 Aug 2019, accepted on 09 Sep 2019 and first published on 10 Sep 2019


Article type: Research Article
DOI: 10.1039/C9QO01009B
Org. Chem. Front., 2019, Advance Article

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    Regio- and stereo-selective decarbonylative alkylative arylation of terminal alkynes with aliphatic aldehydes and arenes via dual C–H bond functionalization

    Y. Peng, F. Zhang, T. Qin, C. Xu and L. Yang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01009B

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