87573-96-4Relevant academic research and scientific papers
Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes
Ghosh, Indrajit,Khamrai, Jagadish,Savateev, Aleksandr,Shlapakov, Nikita,Antonietti, Markus,K?nig, Burkhard
, p. 360 - 366 (2019/08/15)
Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two- or three-component system for direct twofold carbon–hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.
Facile, efficient and eco-friendly synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles
Kuhn, Bruna L.,Fortes, Margiani P.,Kaufman, Teodoro S.,Silveira, Claudio C.
, p. 1648 - 1652 (2014/03/21)
A concise, two-step eco-friendly approach towards the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles, is reported. The synthesis comprises the oxone-mediated thiocyanation of the starting heterocycles towards intermediate 3-thiocyanato indoles and 2-thiocyanato pyrroles, and their subsequent treatment with sodium azide in 2-propanol/water under zinc bromide promotion.
A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole derivatives of indoles and pyrroles employing CeCl3·7H 2O in PEG-400
Fortes, Margiani P.,Bassaco, Mariana M.,Kaufman, Teodoro S.,Silveira, Claudio C.
, p. 34519 - 34530 (2014/11/08)
The use of CeCl3·7H2O in polyethyleneglycol 400 (PEG-400), as an efficient and eco-friendly promoter system for the convenient synthesis of 5-sulfenyl tetrazoles derived from indoles and pyrroles, is reported. The synthesis entails the [3 + 2] cycloaddition reaction of NaN3 with 3-thiocyanato indoles (including 3,3′-di-thiocyanato- 1H,1H′,2,2′-biindoles) and 2-thiocyanato pyrroles. The thiocyanates were conveniently obtained by the oxone-mediated thiocyanation of differently substituted starting indoles, 1H,1H′,2,2′-biindoles and N-aryl pyrroles with NH4SCN. The scope and limitations of the transformation were also studied. This journal is the Partner Organisations 2014.
New data on heteroarene thiocyanation by anodic oxidation of NH 4SCN. the processes of electroinduced nucleophilic aromatic substitution of hydrogen
Kokorekin, Vladimir A.,Sigacheva, Vera L.,Petrosyan, Vladimir A.
supporting information, p. 4306 - 4309 (2014/07/22)
Potentiostatic (galvanostatic) electrolysis of NH4SCN in an undivided cell under mild conditions (25 °C, Pt anode, MeCN) was employed to perform the anodic thiocyanation of nitrogen-containing heterocycles with yields up to 95%. The regularitie
