α-Selective syn-Carbotrifluoromethylthiolation of Alkynes

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Authors
Shah, Prachi
Chaładaj, Wojciech ORCID logo 0000-0001-8143-3788
Date
2025
Journal Title
Journal ISSN
Volume Title
Publisher
American Chemical Society
License
Creative Commons License
Creative Commons Attribution 4.0 International License
Abstract
Trifluoromethylthiolative difunctionalization of alkynes typically proceeds in an anti-fashion delivering the SCF3 group in the β-position (anti-Markovnikov). Herein, we disclose a vicinal syn-arylation-trifluoromethylthiolation of alkynes enabling α-selective introduction of the SCF3 group (Markovnikov). The unique selectivity was achieved via a merge of Ni-catalyzed carbomagnesiation with a subsequent Cu-mediated trifluoromethylthiolation of the resulting vinyl-magnesium species. The former component of the sequential process determines both the regio- and stereoselectivity of the overall transformation.
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Citation
Org. Lett. 2025, 27, 10, 2498–2503 // https://doi.org/10.1021/acs.orglett.5c00570
URI
https://open.icm.edu.pl/handle/123456789/25555
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