Hossain, Asik and Engl, Sebastian and Lutsker, Eugen and Reiser, Oliver (2019) Visible-Light-Mediated Regioselective Chlorosulfonylation of Alkenes and Alkynes: Introducing the Cu(II) Complex [Cu(dap)Cl-2] to Photochemical ATRA Reactions. ACS CATALYSIS, 9 (2). 1103-+. ISSN 2155-5435,
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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)Cl-2] 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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | TRANSFER RADICAL-ADDITION; VINYL SULFONES; STEREOSELECTIVE CHLOROSULFONYLATION; ARENESULFONYL CHLORIDES; TERMINAL ALKYNES; PHOTOREDOX; COPPER; SULFONYLATION; OLEFINS; HALIDES; photocatalysis; copper; ATRA reaction; heterodifunctionalization; sulfone |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 20 Apr 2020 06:36 |
| Last Modified: | 20 Apr 2020 06:36 |
| URI: | https://pred.uni-regensburg.de/id/eprint/27633 |
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