Journal
ACS CATALYSIS
Volume 6, Issue 11, Pages 7335-7339Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b02323
Keywords
C-N activation; amide cross-coupling; cooperative catalysis; C-N cleavage; primary amides
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Funding
- Rutgers University
- NSF-MRI grant [CHE-1229030]
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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.
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