Issue 12, 2016

Suzuki coupling for preparation of allenes – ligand effects and chirality transfer

Abstract

A general and efficient palladium-catalyzed coupling of propargylic carbonates with organoboronic acids has been developed by identifying a commercially available semi-labile bidentated o-(diphenylphosphino)benzaldehyde as the effective ligand affording allenes under a set of very mild reaction conditions. Many functional groups are tolerated in this reaction, and high chirality transfer has also been realized in the presence of water leading to a very rapid reaction for the synthesis of easily racemized 1,3-diarylallenes. A rationale has been proposed to demonstrate the role of the ligand.

Graphical abstract: Suzuki coupling for preparation of allenes – ligand effects and chirality transfer

Supplementary files

Article information

Article type
Research Article
Submitted
26 Aug 2016
Accepted
26 Sep 2016
First published
28 Sep 2016

Org. Chem. Front., 2016,3, 1705-1710

Suzuki coupling for preparation of allenes – ligand effects and chirality transfer

H. Luo, Y. Yu and S. Ma, Org. Chem. Front., 2016, 3, 1705 DOI: 10.1039/C6QO00489J

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