Regiodivergent Synthesis of 4‐ and 5‐Sulfenyl Oxazoles from Alkynyl Thioethers

Chemistry - A European Journal, Год журнала: 2024, Номер 30(40)

Опубликована: Май 14, 2024

The regiodivergent synthesis of 4- and 5-sulfenyl oxazoles from 1,4,2-dioxazoles alkynyl thioethers has been achieved. Gold-catalysed conditions are used to favour the formation via β-selective attack nitrenoid relative sulfenyl group. In contrast, 4-sulfenyl formed by α-selective reaction under Brønsted acid same substrates. nature stabilising gold-sulfur interactions have investigated natural bond orbital analysis, showing that S→Au significantly stronger in intermediate favours oxazoles. A kinetic survey identifies catalyst inhibition processes. This study into methods includes development telescoped annulation-oxidation protocols for regioselective access oxazole sulfoxides sulfones.

Язык: Английский

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2704 - 2707

Опубликована: Окт. 28, 2024

Язык: Английский