68667-88-9Relevant academic research and scientific papers
Cu-Catalyzed photoredox chlorosulfonation of alkenes and alkynes
Alkan-Zambada, Murat,Hu, Xile
, p. 4525 - 4533 (2019)
Visible-light photoredox chlorosulfonation of alkenes and alkynes is achieved using a Cu photocatalyst. The reactions occur under mild conditions, have broad scope, and have high functional group tolerance.
Making Copper Photocatalysis Even More Robust and Economic: Photoredox Catalysis with [CuII(dmp)2Cl]Cl
Engl, Sebastian,Reiser, Oliver
supporting information, p. 1523 - 1533 (2019/07/31)
The CuII complex [CuII(dmp)2Cl]Cl (dmp = 2,9-dimethyl-1,10-phenanthroline) is evaluated as an oxidation stable precursor for visible-light-mediated CuI-photoredox catalysis, being efficient and considerable more cost-effective compared to previously established copper(I) photocatalysts. Its performance and efficiency are demonstrated within a broad scope of atom transfer radical addition (ATRA) reactions, allowing the 1,2-difunctionalization of alkenes, as well as for decarboxylative coupling and an Appel reaction. Moreover, the utility of the complex is shown by various gram-scale functionalizations of styrene, thus suggesting [CuII(dmp)2Cl]Cl to be a low-priced alternative precatalyst for processes run on scale. Furthermore, this study provides UV/Vis evidence on the mechanism for the visible light activation of CuII complexes.
Visible-Light-Mediated Regioselective Chlorosulfonylation of Alkenes and Alkynes: Introducing the Cu(II) Complex [Cu(dap)Cl2] to Photochemical ATRA Reactions
Hossain, Asik,Engl, Sebastian,Lutsker, Eugen,Reiser, Oliver
, p. 1103 - 1109 (2019/02/10)
A visible-light-mediated photocatalyzed protocol utilizing copper-phenanthroline-based catalysts has been developed that can convert a large number of olefins into their chlorosulfonylated products. Besides the Cu(I) complex [Cu(dap)2]Cl, now well-established in photo-ATRA processes, the corresponding Cu(II) complex [Cu(dap)Cl2] proved to be often even more efficient in the title reaction, being advantageous from an economic point of view but also opening up new avenues for photoredox catalysis. Moreover, the copper complexes outperformed commonly used ruthenium, iridium, or organic dye based photocatalysts, owing to their ability to stabilize or interact with transient radicals by inner sphere mechanisms. The use of stoichiometric Na2CO3 in combination with the copper photocatalysts was found to be essential to convert unactivated olefins to the desired products, in contrast to activated olefins for which no additive was required. As suggested by appropriate control experiments, the role of Na2CO3 is attributed to prevention of poisoning of the catalyst.
