Synthesis 2018; 50(12): 2329-2336
DOI: 10.1055/s-0036-1591580
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© Georg Thieme Verlag Stuttgart · New York

Enabling the Rearrangement of Unactivated Allenes to 1,3-Dienes by Use of a Palladium (0)/Boric Acid System

Yassir Al-Jawaheri
a  School of Science, Department of Chemistry, Loughborough University, LE11 3TU, U.K.   Email: M.C.Kimber@lboro.ac.uk
b  College of Education, Department of Chemistry, Mosul University, Iraq
,
Matthew Turner
a  School of Science, Department of Chemistry, Loughborough University, LE11 3TU, U.K.   Email: M.C.Kimber@lboro.ac.uk
,
a  School of Science, Department of Chemistry, Loughborough University, LE11 3TU, U.K.   Email: M.C.Kimber@lboro.ac.uk
› Author Affiliations
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

 
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