Enabling the rearrangement of unactivated allenes to 1,3-dienes by use of a palladium (0)/boric acid system
journal contributionposted on 07.06.2018, 10:38 by yassir Al-Jawaheri, Matthew C. Turner, Marc KimberMarc Kimber
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.
This work was financially supported by Loughborough University. Y.A. acknowledges the Ministry of Higher Education of Iraq for funding.