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Synthesis 2018; 50(12): 2329-2336
DOI: 10.1055/s-0036-1591580
DOI: 10.1055/s-0036-1591580
feature
Enabling the Rearrangement of Unactivated Allenes to 1,3-Dienes by Use of a Palladium (0)/Boric Acid System
This work was financially supported by Loughborough University. Y.A. acknowledges the Ministry of Higher Education of Iraq for funding.Further Information
Publication History
Received: 28 February 2018
Accepted after revision: 04 April 2018
Publication Date:
17 May 2018 (online)
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; using a direct sample loop and flow injection ESI-HRMS analysis we have detected and identified key π-allylpalladium complexes that support the addition of the palladium hydride complex to the allene.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591580.
- Supporting Information
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For representative examples see
For a review on the use of ESI-MS to probe reactive intermediates see:
Also see: