Burykina, Julia V. 
; Shlapakov, Nikita S. ; Gordeev, Evgeniy G. ; König, Burkhard ; Ananikov, Valentine P.
Alternative Links zum Volltext:DOIVerlag
| Dokumentenart: | Artikel |
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| Titel eines Journals oder einer Zeitschrift: | Chemical Science |
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| Verlag: | ROYAL SOC CHEMISTRY |
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| Ort der Veröffentlichung: | CAMBRIDGE |
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| Band: | 11 |
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| Nummer des Zeitschriftenheftes oder des Kapitels: | 37 |
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| Seitenbereich: | S. 10061-10070 |
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| Datum: | 2020 |
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| Institutionen: | Chemie und Pharmazie > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
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| Identifikationsnummer: | | Wert | Typ |
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| 10.1039/d0sc01939a | DOI |
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| Stichwörter / Keywords: | INITIO MOLECULAR-DYNAMICS; DENSITY-MATRIX; BASIS-SETS; GAUSSIAN-ORBITALS; VINYL SULFIDES; BOND FORMATION; ALKYNES; HYDROTHIOLATION; CYCLIZATIONS; ACTIVATION; |
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| Dewey-Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik > 540 Chemie |
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| Status: | Veröffentlicht |
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| Begutachtet: | Ja, diese Version wurde begutachtet |
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| An der Universität Regensburg entstanden: | Ja |
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| Dokumenten-ID: | 49603 |
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Zusammenfassung
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 ...
Zusammenfassung
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.
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