Lanthanide formamidinates as improved catalysts for the Tishchenko reaction

Agustino, Peter W. Roesky, Glen B. Deacon, Kristina Konstas, Peter C. Junk

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

The tris(formamidinato)lanthanum(III) complexes [La(o-TolForm) 3(thf)2] [1; o-TolForm = N,N′-bis(o-tolyl) formamidin-ate], [La(XylForm)3(thf)] [2; XylForm = N,N′-bis(2,6-dimethylphenyl)formamidinate], and [La(EtForm)3] [3, EtForm = N,N′-bis(2,6-diethylphenyl)formamidinate] are a new class of precatalysts for the Tishchenko reaction. Their catalytic activity is a result of their high Lewis acidity and the ease with which the ligand spheres can be interchanged. For the dimerization of benzaldehyde to give benzyl benzoate, which is a benchmark reaction, compound 1 is, to the best of our knowledge, the most active catalyst ever reported. On a preparative scale, the reaction can be performed in the absence of solvent. A range of aromatic, heteroaromatic, and aliphatic aldehydes was rapidly converted into the corresponding esters by using catalysts 1-3.

Original languageEnglish
Pages (from-to)693-697
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number4
DOIs
Publication statusPublished - 12 Feb 2008

Keywords

  • Aldehydes
  • Homogeneous catalysis
  • Lanthanum
  • N ligands
  • Rare-earth formamidinates

Fingerprint Dive into the research topics of 'Lanthanide formamidinates as improved catalysts for the Tishchenko reaction'. Together they form a unique fingerprint.

Cite this