Enabling the rearrangement of unactivated allenes to 1,3-dienes by use of a palladium (0)/boric acid system

Al-Jawaheri, yassir; Turner, Matthew C.; Kimber, Marc

Enabling the rearrangement of unactivated allenes to 1,3-dienes by use of a palladium (0)/boric acid system

journal contribution

posted on 2018-06-07, 10:38 authored 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.

Funding

This work was financially supported by Loughborough University. Y.A. acknowledges the Ministry of Higher Education of Iraq for funding.

History

School

Science

Department

Chemistry

Published in

SYNTHESIS

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.

Publisher

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Acceptance date

2018-04-04

Publication date

2018-05-17

Notes

This paper was accepted for publication in the journal Synthesis and the definitive published version is available at https://doi.org/10.1055/s-0036-1591580.