ATP3 and MTP3: easily prepared stable perruthenate salts for oxidation applications in synthesis

Moore, Peter W., Read, Christopher D. G., Bernhardt, Paul V. and Williams, Craig M. (2018) ATP3 and MTP3: easily prepared stable perruthenate salts for oxidation applications in synthesis. Chemistry: A European Journal, 24 18: 4556-4561. doi:10.1002/chem.201800531


Author Moore, Peter W.
Read, Christopher D. G.
Bernhardt, Paul V.
Williams, Craig M.
Title ATP3 and MTP3: easily prepared stable perruthenate salts for oxidation applications in synthesis
Journal name Chemistry: A European Journal   Check publisher's open access policy
ISSN 1521-3765
0947-6539
Publication date 2018-03-06
Year available 2018
Sub-type Article (original research)
DOI 10.1002/chem.201800531
Open Access Status Not yet assessed
Volume 24
Issue 18
Start page 4556
End page 4561
Total pages 6
Place of publication Weinheim, Germany
Publisher Wiley - V C H Verlag GmbH & Co. KGaA
Language eng
Abstract The Ley-Griffith tetra-n-propylammonium perruthenate (TPAP) catalyst has been widely deployed by the synthesis community, mainly for the oxidation of alcohols to aldehydes and ketones, but also for a variety of other synthetic transformations (e.g. diol cleavage, isomerizations, imine formation and heterocyclic synthesis). Such popularity has been forged on broad reaction scope, functional group tolerance, mild conditions, and commercial catalyst supply. However, the mild instability of TPAP creates preparation, storage, and reaction reproducibility issues, due to unpreventable slow decomposition. In search of attributes conducive to catalyst longevity an extensive range of novel perruthenate salts were prepared. Subsequent evaluation unearthed a set of readily synthesized, bench stable, phosphonium perruthenates (ATP3 and MTP3) that mirror the reactivity of TPAP, but avoid storage decomposition issues.
Formatted abstract
The Ley-Griffith tetra-n-propylammonium perruthenate (TPAP) catalyst has been widely deployed by the synthesis community, mainly for the oxidation of alcohols to aldehydes and ketones, but also for a variety of other synthetic transformations (e.g. diol cleavage, isomerizations, imine formation and heterocyclic synthesis). Such popularity has been forged on broad reaction scope, functional group tolerance, mild conditions, and commercial catalyst supply. However, the mild instability of TPAP creates preparation, storage, and reaction reproducibility issues, due to unpreventable slow decomposition. In search of attributes conducive to catalyst longevity an extensive range of novel perruthenate salts were prepared. Subsequent evaluation unearthed a set of readily synthesized, bench stable, phosphonium perruthenates (ATP3 and MTP3) that mirror the reactivity of TPAP, but avoid storage decomposition issues.
Keyword Ley-Griffith oxidation
TPAP
Alcohol oxidation
Aldehydes
Perruthenate
Q-Index Code C1
Q-Index Status Provisional Code
Grant ID DP160102887
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: HERDC Pre-Audit
School of Chemistry and Molecular Biosciences
 
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Created: Wed, 14 Mar 2018, 10:08:01 EST