Cannizzaro-Type Disproportionation of Aromatic Aldehydes to Amides and Alcohols by Using Either a Stoichiometric Amount or a Catalytic Amount of Lanthanide Compounds
- 16 March 2006
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (8), 3149-3153
- https://doi.org/10.1021/jo060063l
Abstract
Aromatic aldehydes can be directly converted to the corresponding amides and alcohols in good to excellent yields by the treatment of aromatic aldehydes with lithium amide LiN(SiMe3)2 in the presence of catalytic lanthanide chlorides LnCl3 or by the treatment of aromatic aldehydes with a stoichiometric amount of lanthanide amides [(Me3Si)2N]3Ln(μ-Cl)Li(THF)3 at ambient temperature. The effects of solvents, substitutents on the phenyl ring, and lanthanide metals on the reaction have been examined. The mechanism of the disproportionation reaction was proposed based on the experimental results.Keywords
This publication has 20 references indexed in Scilit:
- Lanthanide amidesPublished by Springer Nature ,2005
- A solvent-free synthesis of α,α′-bis(substituted benzylidene) cycloalkanones catalyzed by lanthanide amides [(Me3Si)2N]3Ln(µ-Cl)Li(THF)3 under microwave irradiationGreen Chemistry, 2005
- Alkene and Diene Hydrosilylations Catalyzed by Lanthanum Tris[bis(trimethylsilyl)amide]Organometallics, 2003
- Direct Conversion of Aldehydes to Amides, Tetrazoles, and Triazines in Aqueous Media by One-Pot Tandem ReactionsThe Journal of Organic Chemistry, 2002
- Solvent-Free and One-Step Beckmann Rearrangement of Ketones and Aldehydes by Zinc OxideSynthesis, 2002
- Organolanthanide-Based Coordination and Insertion Reactivity of the Anion Formed by Deprotonation of ε-CaprolactamOrganometallics, 2001
- Controlled Ring-Opening Polymerization of ε-Caprolactone Promoted by “in Situ” Formed Yttrium AlkoxidesMacromolecules, 2000
- Homoleptische Lanthanoidamide als Homogenkatalysatoren für die Tischtschenko-ReaktionAngewandte Chemie, 1998
- Chiral Lanthanocene Derivatives Containing Two Linked Amido−Cyclopentadienyl Ligands: Heterobimetallic Structure and Lactone Polymerization ActivityOrganometallics, 1997
- Progress in hydroformylation and carbonylationJournal of Molecular Catalysis A: Chemical, 1995