Abstract
Palladium-catalyzed Suzuki−Miyaura cross-coupling of primary benzamides enabled by a merger of site-selective N,N-di-Boc-activation and cooperative catalysis via N−C bond cleavage for the synthesis of biaryl ketones is reported. We present the synergistic combination of Lewis base and palladium catalysis as a concept to activate inert amide N−C bonds. The mild reaction conditions provide a direct route to structurally diverse ketones. The reaction tolerates a wide range of electrophilic functional groups. Considering the fundamental importance of primary amides as pharmaceutical and synthetic intermediates, the strategy has a potential for developing a diverse array of valuable amide N−C bond functionalization reactions by the synergistic merger of Lewis base and organometallic catalysis.
| Original language | American English |
|---|---|
| Pages (from-to) | 7335-7339 |
| Number of pages | 5 |
| Journal | ACS Catalysis |
| Volume | 6 |
| Issue number | 11 |
| DOIs | |
| State | Published - Nov 4 2016 |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
Keywords
- Amide cross-coupling
- Cooperative catalysis
- C−N activation
- C−N cleavage
- Primary amides
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