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- Title
Activation of α-Diazocarbonyls by Organic Catalysts: Diazo Group Acting as a Strong N-Terminal Electrophile.
- Authors
Li, Lei; Chen, Jia ‐ Jia; Li, Yi ‐ Jin; Bu, Xiu ‐ Bin; Liu, Qun; Zhao, Yu ‐ Long
- Abstract
For the first time α-diazocarbonyls have been used as highly active N-terminal electrophiles in the presence of bicyclic amidine catalysts. The CN bond-forming reactions of active methylene compounds as C nucleophiles with α-diazocarbonyls as N-terminal electrophiles proceed quickly under ambient conditions, in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), because of the formation of the reactive N-terminal electrophilic intermediates. DBU activates both the active methylene and α-diazocarbonyl. Importantly, this reaction is general for both active methylenes and α-diazocarbonyls, and the activation mode will lead to new synthetic applications of α-diazocarbonyls.
- Subjects
CARBENES; NUCLEOPHILES; CONDENSATION; RING formation (Chemistry); NUCLEAR magnetic resonance
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 41, p12275
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201505064