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- Title
N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Alkenes/ α-Bromoacetophenones with Aldehydes: A Facile Entry to α,β-Epoxy Ketones.
- Authors
Reddi, Rambabu N.; Prasad, Pragati K.; Sudalai, Arumugam
- Abstract
A novel, N-heterocyclic carbene (NHC) catalyzed direct oxidative coupling of styrenes with aldehydes has been described for the synthesis of a,b-epoxy ketones in good yields. This unprecedented regioselective oxidative coupling employs NBS/DBU/DMSO (DBU=1,8-diazabicyclo [5.4. 0] undec-7- ene, DMSO=dimethylsulfoxide, NBS=N-bromosuccinimide) as an oxidative system at ambient conditions. Additionally, first NHC-catalyzed Darzens reaction of a-bromoketones and aldehydes under mild reaction conditions has also been described. Interestingly, mechanistic studies have revealed the preferred reactivity of NHC with alkene/a-bromoketone rather than aldehydes, thus proceeding via the ketodeoxy Breslow intermediate.
- Subjects
CARBENE synthesis; ACETOPHENONE synthesis; EPOXIDATION; KETONE synthesis; OXIDATIVE coupling; ALDEHYDE synthesis
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 47, p14356
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201507363