Abderrazak, Youssef and Reiser, Oliver (2024) Copper Photocatalyzed Divergent Access to Organic Thio- and Isothiocyanates. ACS CATALYSIS, 14 (7). pp. 4847-4855. ISSN 2155-5435,
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We disclose a copper-photocatalyzed strategy that enables selective access to organic thiocyanates and isothiocyanates using benzylic thiocyanates as ATRA reagents. The electronic nature of the aromatic system is a crucial factor defining the outcome of the reaction for forging either the kinetic C-S or the thermodynamic C-N bonds. Mechanistic investigations support a radical pathway initiated by a reductive C-S bond cleavage of the substrates followed by a divergent inner-/outer-sphere interaction with copper depending on the electronic density of the formed intermediates. The developed protocol proceeds with high regio- and chemoselectivity and can also be applied for late-stage functionalization of bioactive molecules. The utility of the products is highlighted by their facile conversion to several building blocks that are relevant to organic synthesis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ALPHA-FLUORINATED ETHERS; THIOCYANATE; COMPLEXES; LIGHT; REDUCTION; ALKENES; THIOETHERS; CHEMISTRY; AMINES; copper; photocatalysis; ATRA; difunctionalization; thiocyanation |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 23 Jul 2025 06:54 |
| Last Modified: | 23 Jul 2025 06:54 |
| URI: | https://pred.uni-regensburg.de/id/eprint/63574 |
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