Synthesis of 1,3-Dienes via a sequential Suzuki-Miyaura coupling/Palladium-mediated Allene isomerization sequence.
journal contributionposted on 18.07.2016 by yassir Al-Jawaheri, Marc Kimber
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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.