Copper- and Photoredox-Catalyzed Cascade to Trifluoromethylated Divinyl Sulfones

Petek, Nejc and Brodnik, Helena and Reiser, Oliver and Stefane, Bogdan (2022) Copper- and Photoredox-Catalyzed Cascade to Trifluoromethylated Divinyl Sulfones. JOURNAL OF ORGANIC CHEMISTRY, 88 (10). pp. 6538-6547. ISSN 0022-3263, 1520-6904

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Abstract

A Cu(I)-photoredox-catalyzed trifluoromethylchlorosulfonylation reaction of terminal alkynes under visible light conditions was developed, giving rise to trifluoromethyl-substituted vinylsulfonyl chlorides, which can subsequently be coupled to a second alkyne under photocatalytic conditions. The transformation proceeds with high regio-and stereoselectivity and can be applied to aliphatic and aromatic alkynes with various functional groups. Trifluoromethyl-substituted divinyl sulfones prepared by this protocol can be readily used as synthetically valuable intermediates as demonstrated with various postmodification examples.

Item Type: Article
Uncontrolled Keywords: CHLOROTRIFLUOROMETHYLATION; COMPLEXES; CHLORIDES; FLUORINE; ALKYNES;
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: 01 Feb 2024 13:41
Last Modified: 01 Feb 2024 13:41
URI: https://pred.uni-regensburg.de/id/eprint/57252

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