401514-40-7Relevant articles and documents
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).
One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes, and Allylamines to Access 2,3-Dihydro-1 H-imi-dazo[1,2-a]indoles
Jin, Hongwei,Liu, Daohong,Liu, Yunkui,Zhou, Bingwei
supporting information, p. 1417 - 1424 (2020/04/27)
A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1 H-imidazo-[1,2-a]indoles in moderate yields is reported. Four C-N bonds are constructed- by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process.
Visible Light-Catalyzed Decarboxylative Alkynylation of Arenediazonium Salts with Alkynyl Carboxylic Acids: Direct Access to Aryl Alkynes by Organic Photoredox Catalysis
Yang, Liangfeng,Li, Haifeng,Du, Yijun,Cheng, Kai,Qi, Chenze
, p. 5030 - 5041 (2019/11/03)
A convenient method mediated by photoredox catalysis is developed for the direct construction of aryl alkynes. Readily available aromatic diazonium salts have been utilized as the aryl radical source to couple alkynyl carboxylic acids to feature the decarboxylative arylation. A wide range of substrates are amenable to this protocol with broad functional group tolerance, and diversely-functionalized aryl alkynes could be synthesized under mild, neutral and transition metal-free reaction conditions using visible light irradiation. Alongside synthetic sustainability associated with the photocatalytic and transition metal-free operation, another key point of this method is that the organic dye catalyst acts as an excited-state reductant, thus establishing the quenching cycle for radical addition and decarboxylative elimination. (Figure presented.).