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

Yassir Al-Jawaheri; Matthew Turner; Marc C. Kimber

doi:10.1055/s-0036-1591580

Synthesis, Table of Contents

Synthesis 2018; 50(12): 2329-2336
DOI: 10.1055/s-0036-1591580

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

Yassir Al-Jawaheri

^aSchool of Science, Department of Chemistry, Loughborough University, LE11 3TU, U.K. Email: M.C.Kimber@lboro.ac.uk

^bCollege of Education, Department of Chemistry, Mosul University, Iraq

,

Matthew Turner

^aSchool of Science, Department of Chemistry, Loughborough University, LE11 3TU, U.K. Email: M.C.Kimber@lboro.ac.uk

,

Marc C. Kimber *

^aSchool of Science, Department of Chemistry, Loughborough University, LE11 3TU, U.K. Email: M.C.Kimber@lboro.ac.uk

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Abstract

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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.

Key words

allene - 1,3-diene - palladium - boric acid - palladium hydride complex

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References

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Supplementary Material

Supporting Information