38940-44-2Relevant academic research and scientific papers
Organocatalytic Three-Component 1,2-Cyanoalkylacylation of Alkenes via Radical Relay
Gao, Yu,Quan, Yusheng,Li, Zhenjiang,Gao, Luoyu,Zhang, Zhihao,Zou, Xin,Yan, Rui,Qu, Yuanyuan,Guo, Kai
, p. 183 - 189 (2021)
Here, we report an unprecedented regioselective, intermolecular 1,2-cyanoalkylacylation of feedstock alkenes with readily available oxime esters and aldehydes by N-heterocyclic carbene (NHC) organocatalysis. The crux of this success is the exquisite control over the radical relay process by an NHC organocatalyst. This protocol offers a general platform for diversity-oriented synthesis of valuable ketonitriles under mild, transition-metal-free, and redox-neutral conditions and highlights its potential in the late-stage functionalization of pharmaceutical architectures and natural products.
C?C bond acylation of oxime ethers via NHC catalysis
Yang, Hai-Bin,Wan, Dan-Hong
supporting information, p. 1049 - 1053 (2021/02/01)
An N-heterocyclic carbene (NHC)-catalyzed strategy has been developed to address the issue of using toxic transitional metals in the field of C?C bond activation. The novel reaction mode enables an efficient docking between the cyanoalkyl from the cycloketone oxime derivative and the acyl group from the aldehyde, affording ketonitrile in moderate to good yields, which is one kind of useful building block for synthesizing nitrogen-containing pharmacophores.
Photocatalytic, Phosphoranyl Radical-Mediated N-O Cleavage of Strained Cycloketone Oximes
Xia, Peng-Ju,Ye, Zhi-Peng,Hu, Yuan-Zhuo,Song, Dan,Xiang, Hao-Yue,Chen, Xiao-Qing,Yang, Hua
supporting information, p. 2658 - 2662 (2019/04/25)
A photoinduced, phosphoranyl radical-mediated protocol for the direct N-O cleavage of strained cycloketone oximes via a polar/SET crossover process was developed for the first time. This visible-light-driven direct N-O activation mode for oxime offers beneficial features such as streamlined synthetic process and versatile photochemical reactivities. Consequently, the alkenes and α-trifluoromethyl alkenes with varied electronic and structural features acted as competent radical receptors in this protocol, enabling facile accesses to a range of elongated cyano and/or gem-difluoroalkene-bearing compounds.
