Burykina, Julia and Shlapakov, Nikita S. and Gordeev, Evgeniy G. and Koenig, Burkhard and Ananikov, Valentine P. (2020) Selectivity control in thiol-yne click reactions via visible light induced associative electron upconversion. CHEMICAL SCIENCE, 11 (37). pp. 10061-10070. ISSN 2041-6520, 2041-6539
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An associative electron upconversion is proposed as a key step determining the selectivity of thiol-yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products - four types of vinyl sulfides were prepared in high yields and selectivity. We report practically important transition-metal-free regioselective thiol-yne addition and formation of the demanding Markovnikov-type product by a radical photoredox process. The photochemical process was directly monitored by mass-spectrometry in a specially designed ESI-MS device with green laser excitation in the spray chamber. The proposed reaction mechanism is supported by experiments and DFT calculations.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | INITIO MOLECULAR-DYNAMICS; DENSITY-MATRIX; BASIS-SETS; GAUSSIAN-ORBITALS; VINYL SULFIDES; BOND FORMATION; ALKYNES; HYDROTHIOLATION; CYCLIZATIONS; ACTIVATION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 12 Mar 2021 07:27 |
| Last Modified: | 12 Mar 2021 07:27 |
| URI: | https://pred.uni-regensburg.de/id/eprint/43597 |
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