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Title: Enabling the rearrangement of unactivated allenes to 1,3-dienes by use of a palladium (0)/boric acid system
Authors: Al-Jawaheri, Yassir
Turner, Matthew C.
Kimber, Marc C.
Keywords: Allene
1,3-diene
Palladium
Boric acid
Palladium-hydride
Issue Date: 2018
Publisher: © Thieme Publishing
Citation: AL-JAWAHERI, Y., TURNER, M.C. and KIMBER, M.C., 2018. Enabling the rearrangement of unactivated allenes to 1,3-dienes by use of a palladium (0)/boric acid system. Synthesis, 50(12), pp. 2329-2336.
Abstract: A redox neutral rearrangement of an allene to a 1,3-diene by means of a unique palladium hydride complex is reported. The palladium hydride complex is generated from a simple Pd0 source and boric acid (B(OH)3), which is typically identified as a waste by-product of the Suzuki-Miyaura reaction. A mechanism for this transformation, using this novel palladium hydride complex is presented; and using direct sample loop and flow injection ESI-HR-MS analysis we have detected and identified key π-allylpalladium complexes, that support the addition of the palladium hydride complex to the allene.
Description: This paper is in closed access until 17th May 2019.
Sponsor: This work was financially supported by Loughborough University. Y.A. acknowledges the Ministry of Higher Education of Iraq for funding.
Version: Accepted for publication
DOI: 10.1055/s-0036-1591580
URI: https://dspace.lboro.ac.uk/2134/33343
Publisher Link: https://doi.org/10.1055/s-0036-1591580
ISSN: 0039-7881
Appears in Collections:Closed Access (Chemistry)

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