Cannizzaro-type disproportionation of aromatic aldehydes to amides and alcohols by using either a stoichiometric amount or a catalytic amount of lanthanide compounds.
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(mu-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.
Zhang
Lijun
L
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.
Wang
Shaowu
S
Zhou
Shuangliu
S
Yang
Gaosheng
G
Sheng
Enhong
E
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D028581:Lanthanoid Series Elements / Q000737:chemistry*; D008670:Metals / Q000737:chemistry; D015394:Molecular Structure
D000438:Alcohols; D000447:Aldehydes; D000577:Amides; D028581:Lanthanoid Series Elements; D008670:Metals