24246-87-5Relevant articles and documents
A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot strategy
Wei, Ting,Zeng, Yongming,He, Wei,Geng, Lili,Hong, Liang
, p. 383 - 385 (2018/04/11)
A facile transformation of alkynes into α-amino ketones by an N-bromosuccinimide-mediated one-pot cascade strategy is described. A variety of α-amino ketones are obtained in moderate to good yields under mild conditions. To overcome the multi-step synthesis, N-bromosuccinimide is involved in multiple tasks, playing a key role in the reaction course.
Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide-dimethyl sulfoxide combination: A facile synthesis of α-amino-ketones and esters
Prasad, Pragati K.,Reddi, Rambabu N.,Sudalai, Arumugam
supporting information, p. 500 - 503 (2016/02/18)
An unprecedented conversion of alkenes and enol ethers to the corresponding α-imido carbonyl compounds with excellent regioselectivity and yields has been developed. This oxo-amination process employs readily available N-bromosuccinimide (NBS) and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant and also leads to the production of amino alcohols in a single step on reduction, thus broadening the scope of this operationally simple reaction. For the first time, the formation of reactive Me2S+-O-Br species generated by the interaction of NBS with DMSO has been proven.
N-Heterocyclic Carbene Catalyzed Oxidative Coupling of Alkenes/ α-Bromoacetophenones with Aldehydes: A Facile Entry to α,β-Epoxy Ketones
Reddi, Rambabu N.,Prasad, Pragati K.,Sudalai, Arumugam
supporting information, p. 14150 - 14153 (2016/01/25)
A novel, N-heterocyclic carbene (NHC) catalyzed direct oxidative coupling of styrenes with aldehydes has been described for the synthesis of α,β-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 α-bromoketones and aldehydes under mild reaction conditions has also been described. Interestingly, mechanistic studies have revealed the preferred reactivity of NHC with alkene/α-bromoketone rather than aldehydes, thus proceeding via the ketodeoxy Breslow intermediate.