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Issue 12, 2016
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Suzuki coupling for preparation of allenes – ligand effects and chirality transfer

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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

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Supplementary files

Article information


Submitted
26 Aug 2016
Accepted
26 Sep 2016
First published
28 Sep 2016

Org. Chem. Front., 2016,3, 1705-1710
Article type
Research Article

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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