[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.
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| http://dx.doi.org/10.1021/ol0494459 | DOI Listing |
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Synthesis of carboxamides by LDA-catalyzed Haller-Bauer and Cannizzaro reactions.
Org Lett
June 2004
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
[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.
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