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1.
J Org Chem ; 89(5): 3049-3057, 2024 Mar 01.
Article in English | MEDLINE | ID: mdl-38332634

ABSTRACT

Peroxygenated compounds have wide applications in various fields, including chemistry, pharmaceutical chemistry, medicine, and materials science. However, there is still a need for more efficient and environmentally friendly synthesis methods for such compounds. Herein, we investigated the two-step, one-pot, regioselective synthesis of α/ß-aromatic peroxy thiols. We explored various substrates and solvents for the reaction and identified the optimal reaction conditions. We successfully obtained several peroxy thiols in moderate to good yields via the selective generation of effective intermediates of iodoalkyl peroxides at room temperature without the need for metal catalysts.

2.
Org Biomol Chem ; 22(10): 2075-2080, 2024 Mar 06.
Article in English | MEDLINE | ID: mdl-38363158

ABSTRACT

The installation of selenium groups has become an essential step across a number of industries such as agrochemicals, drug discovery, and materials. However, direct C(sp3)-H selenation, which is most atom economical, remains a formidable challenge, and only a few examples have been reported to date. In this article, we introduce the transition metal-free C(sp3)-H selenation with the easily available ß-ketosulfones and diselenides as the material source. This benign protocol permits access to a broad spectrum of α-aryl(alkyl) seleno-ß-ketosulfones in high yields with outstanding functional group compatibility. Distinct advantages of this protocol over all previous methods encompass the utilization of base and air as an oxidant, room temperature, and enhanced green chemistry matrices.

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