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Title: Synthesis of 1,3-Dienes via a sequential Suzuki-Miyaura coupling/Palladium-mediated Allene isomerization sequence.
Authors: Al-Jawaheri, Yassir
Kimber, Marc C.
Issue Date: 2016
Publisher: © American Chemical Society
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.
Abstract: 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.
Description: 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
Version: Accepted for publication
DOI: 10.1021/acs.orglett.6b01841
URI: https://dspace.lboro.ac.uk/2134/21992
Publisher Link: http://dx.doi.org/10.1021/acs.orglett.6b01841
ISSN: 1523-7060
Appears in Collections:Published Articles (Chemistry)

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