Journal
ACS CATALYSIS
Volume 9, Issue 9, Pages 8171-8177Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b02440
Keywords
C-N activation; ruthenium; anilines; carbon-nitrogen cleavage; cross-coupling
Categories
Funding
- Rutgers University
- NSF [CAREER CHE-1650766]
- ACS PRF [DNI-55549]
- China Scholarship Council [201808610096]
- NSF -MM grant [CHE-1229030]
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Selective activation of neutral carbon-nitrogen bonds is of great synthetic importance, because amines are among the most prevalent motifs across organic and bioactive molecules. Herein, we report the Ru(0)-catalyzed selective cleavage of neutral C(aryl)-N bonds in generic aniline derivatives enabled by a combination of Ru-3(CO)(12) and an imino auxiliary. These mild conditions provide a direct route to high-value biaryl ketones and biaryl aldehydes after facile in situ hydrolysis. A broad range of organoboranes and anilines can be coupled with high C-N cleavage selectivity. Most crucially, the reaction achieves exquisite selectivity for activation of C(aryl)-N bonds in the presence of typically more kinetically favorable Caryl)-H bonds. The method provides a strategy for the construction of functionalized terphenyls by exploiting orthogonal properties of the Ru(0) catalyst system and traceless nucleophilic properties of anilines.
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