Issue 20, 2023

Visible-light-induced dehydrogenative β-trifluoromethylthiolation of tertiary amines and direct β-trifluoromethylthiolation of enamides

Abstract

Facilitated by electron donor–acceptor complexes, an efficient dehydrogenative β-trifluoromethylthiolation of tertiary amines with N-trifluoromethylthiophthalimide is presented under transition-metal-free, external oxidant-free, photocatalyst-free and mild reaction conditions. This protocol accommodates a range of substituted piperidines, as well as seven- and eight-membered saturated heterocycles. Additionally, employing this photocatalyst-free approach, direct β-trifluoromethylthiolation of electron-rich enamides was also achieved through the involvement of a photoactive electron donor–acceptor (EDA) complex.

Graphical abstract: Visible-light-induced dehydrogenative β-trifluoromethylthiolation of tertiary amines and direct β-trifluoromethylthiolation of enamides

Supplementary files

Article information

Article type
Research Article
Submitted
04 Aug 2023
Accepted
14 Sep 2023
First published
14 Sep 2023

Org. Chem. Front., 2023,10, 5284-5290

Visible-light-induced dehydrogenative β-trifluoromethylthiolation of tertiary amines and direct β-trifluoromethylthiolation of enamides

Y. Song, Z. Jiang, Y. Zhu, T. Sun, X. Xia and D. Wang, Org. Chem. Front., 2023, 10, 5284 DOI: 10.1039/D3QO01231J

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