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URN to cite this document: urn:nbn:de:bvb:703-epub-8385-0
Title data
Zhang, Tong ; Rabeah, Jabor ; Das, Shoubhik:
Red-light-mediated copper-catalyzed photoredox catalysis promotes regioselectivity switch in the difunctionalization of alkenes.
In: Nature Communications.
Vol. 15
(2024)
.
- 5208.
ISSN 2041-1723
DOI der Verlagsversion: https://doi.org/10.1038/s41467-024-49514-4
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Abstract
Controlling regioselectivity during difunctionalization of alkenes remains a significant challenge, particularly when the installation of both functional groups involves radical processes. In this aspect, methodologies to install trifluoromethane (−CF₃) via difunctionalization have been explored, due to the importance of this moiety in the pharmaceutical sectors; however, these existing reports are limited, most of which affording only the corresponding β-trifluoromethylated products. The main reason for this limitation arises from the fact that −CF₃ group served as an initiator in those reactions and predominantly preferred to be installed at the terminal (β) position of an alkene. On the contrary, functionalization of the −CF₃ group at the internal (α) position of alkenes would provide valuable products, but a meticulous approach is necessary to win this regioselectivity switch. Intrigued by this challenge, we here develop an efficient and regioselective strategy where the −CF₃ group is installed at the α-position of an alkene. Molecular complexity is achieved via the simultaneous insertion of a sulfonyl fragment (−SO₂R) at the β-position. A precisely regulated sequence of radical generation using red light-mediated photocatalysis facilitates this regioselective switch from the terminal (β) position to the internal (α) position. Furthermore, this approach demonstrates broad substrate scope and industrial potential for the synthesis of pharmaceuticals under mild reaction conditions.
Further data
| Item Type: | Article in a journal |
|---|---|
| DDC Subjects: | 500 Science > 540 Chemistry |
| Institutions of the University: | Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I - Photo- und Elektrokatalyse für Nachhaltigkeit > Chair Organic Chemistry I - Photo- und Elektrokatalyse für Nachhaltigkeit - Univ.-Prof. Dr. Shoubhik Das Faculties Faculties > Faculty of Biology, Chemistry and Earth Sciences Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I - Photo- und Elektrokatalyse für Nachhaltigkeit |
| Language: | English |
| Originates at UBT: | Yes |
| URN: | urn:nbn:de:bvb:703-epub-8385-0 |
| Date Deposited: | 01 Apr 2025 08:51 |
| Last Modified: | 01 Apr 2025 08:53 |
| URI: | https://epub.uni-bayreuth.de/id/eprint/8385 |
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