Synthesis of carboxamides by LDA-catalyzed Haller-Bauer and Cannizzaro reactions.
[reaction: see text] The first direct synthesis of N-alkylcarboxamides and N,N-dialkylcarboxamides by Haller-Bauer (HB) and Cannizzaro-type reactions has been realized. Lithium N,N-diisopropylamide (LDA) catalyst was successfully used in not only the HB reaction of benzylic ketones with lithium N-alkylamides to give the corresponding carboxamides and hydrocarbons but also in the Cannizzaro-type reaction of aldehydes with lithium N-alkylamides or lithium N,N-dialkylamides to give the corresponding carboxamides and alcohols.
Ishihara
Kazuaki
K
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan. ishihara@cc.nagoya-u.ac.jp
Yano
Takayuki
T
D000577:Amides / Q000138:chemical synthesis*; D002384:Catalysis; D018020:Lithium Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*
D000577:Amides; D018020:Lithium Compounds; D009942:Organometallic Compounds