Issue 20, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
13 Aug 2019
Accepted
09 Sep 2019
First published
10 Sep 2019

Org. Chem. Front., 2019,6, 3597-3602

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, 6, 3597 DOI: 10.1039/C9QO01009B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements