16215-12-6Relevant articles and documents
Shanmuganathan,Subramanian
, p. 911 (1967)
Intermolecular [2 + 2] Photocycloaddition of α,β-Unsaturated Sulfones: Catalyst-Free Reaction and Catalytic Variants
Jeremias, Noah,Mohr, Lisa-Marie,Bach, Thorsten
supporting information, p. 5674 - 5678 (2021/08/03)
2-Aryl-1-sulfonyl-substituted cyclobutanes were prepared in an intermolecular [2 + 2] photocycloaddition from various α,β-unsaturated sulfones and olefins upon irradiation at λ = 300 nm (26 examples, 60-99% yield). Lewis acids catalyzed the [2 + 2] photocycloaddition of 2-benzimidazolyl styryl sulfones. At short wavelengths, the latter substrates underwent C-S bond cleavage but AlBr3 (5 mol %) allowed for an intermolecular reaction with 2,3-dimethyl-2-butene at longer wavelengths. A chiral-at-metal Lewis acid (2 mol %) facilitated an enantioselective reaction (up to 77% ee).
Electrochemical sulfonylation of alkenes with sulfonyl hydrazides: A metal- And oxidant-free protocol for the synthesis of (: E)-vinyl sulfones in water
Cai, Jianpeng,Guo, Huishi,Lai, Yin-Long,Liao, Jianhua,Luo, Jianmin,Mo, Yunyan,Yan, Shaoxi,Zhang, Shengling,Zhu, Lejie
, p. 33155 - 33160 (2020/10/05)
An efficient electrochemical transformation of a variety of alkenes and sulfonyl hydrazides into vinyl sulfones with a catalytic amount of tetrabutylammonium iodide in water is reported. The reaction proceeds smoothly to afford vinyl sulfones with good selectivities and yields at room temperature under air in an undivided cell. Cyclic voltammograms and control experiments have been performed to provide preliminary insight into the reaction mechanism. The key features of this reaction include using pure water as solvent, transition metal- and oxidant-free conditions, and being easily scaled up to gram-scale synthesis. This journal is
