1058258-49-3Relevant academic research and scientific papers
Photoinduced three-component reactions of tetracyanobenzene with alkenes in the presence of 1,3-dicarbonyl compounds as nucleophiles
Lu, Zhi-Feng,Shen, Yong-Miao,Yue, Jia-Jun,Hu, Hong-Wen,Xu, Jian-Hua
supporting information; body text, p. 8010 - 8015 (2009/04/11)
(Chemical Equation Presented) Photoinduced three-component reactions between tetracyanobenzene (TCNB), an aromatic olefin, and a β-dicarbonyl compound afford products composed of the three components via formal elimination of hydrogen cyanide, leading to the vicinal dialkylation of the olefin and the α-alkylation of the β-dicarbonyl compounds. It is shown that these reactions are initiated by photoinduced electron transfer (PET) from the olefin to the singlet excited TCNB and proceed by a nucleophile-olefin combination, aromatic substitution (NOCAS) reaction sequence with the enolized β-dicarbonyl compound as a nucleophile. Therefore, aromatic olefins are suitable substrates in photo-NOCAS reactions when TCNB is used as the electron acceptor. In addition, these results show that the enol of β-dicarbonyl compound serves as a carbon nucleophile to trap the alkene cation radical in PET reactions to lead to C-C bond formation.
