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Synthesis of 1,3-Dienes via a sequential Suzuki-Miyaura coupling/Palladium-mediated Allene isomerization sequence.

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posted on 18.07.2016 by yassir Al-Jawaheri, Marc Kimber
We report a facile method for the synthesis of 1,3-dienes by a sequential process consisting of a palladium catalyzed, base-free, Suzuki-Miyaura coupling/isomerization sequence. This sequence couples boronic acids with propargyl alcohols, generating the requisite allene in situ, followed by conversion of the unactivated allene to its 1,3-diene via a hydro-palladation/dehydro-palladation process. This process is general for a range of boronic acids, including boronic acids with electron donating and withdrawing groups, as well as heteroarylboronic acids. Key to this process is the boric acid by-product of the base-free Suzuki–Miyauru coupling, which generates the required palladium–hydrido complex [H-PdII-OB(OH)2] required for the isomerization.

History

School

  • Science

Department

  • Chemistry

Published in

Organic Letters

Citation

AL-JAWAHERI, Y. and KIMBER, M.C., 2016. Synthesis of 1,3-Dienes via a sequential Suzuki-Miyaura coupling/Palladium-mediated Allene isomerization sequence. Organic Letters, 18(14), pp 3502–3505.

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© American Chemical Society

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Acceptance date

30/06/2016

Publication date

2016

Notes

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.orglett.6b01841. Its reuse is subject to the ACS terms and conditions http://pubs.acs.org/page/policy/authorchoice_termsofuse.html

ISSN

1523-7060

Language

en

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