Aryl iodane-induced cascade arylation–1,2-silyl shift–heterocyclization of propargylsilanes under copper catalysis
Beilstein journal of organic chemistry 2025
Rasma Kroņkalne, Rūdolfs Beļaunieks, Armands Sebris, Anatoly Mishnev, Māris Turks

A novel copper-catalyzed arylation strategy for propargylsilanes utilizing diaryl-λ3-iodanes has been developed, enabling a cascade sequence involving 1,2-silyl migration and heterocyclization. The β-silicon effect facilitates the formation of stabilized allyl cation intermediates that undergo regioselective trapping by internal O- and N-nucleophiles furnishing functionalized heterocycles. This method provides access to tetrahydrofuran or pyrrolidine frameworks, each bearing a trifunctionalized (E)-configured vinyl side chain. The use of a shorter linker provides entry to 1,2,3,6-tetrahydropyridines. Additionally, in the absence of internal nucleophiles, this methodology yields aryl-substituted 1,3-dienes. This work introduces a palladium-free, single-step alternative to multistep heterocycle construction from propargylsilanes and highlights the synthetic potential of iodane-mediated carbofunctionalization under copper catalysis.


Keywords
arylation reactions; copper-catalysis; iodanes; propargylsilanes; 1,2-silyl shift
DOI
10.3762/bjoc.21.154
Hyperlink
https://www.beilstein-journals.org/s/c237ywuUrl

Kroņkalne, R., Beļaunieks, R., Sebris, A., Mishnev, A., Turks, M. Aryl iodane-induced cascade arylation–1,2-silyl shift–heterocyclization of propargylsilanes under copper catalysis. Beilstein journal of organic chemistry, 2025, Vol. 21, pp.1984-1994. Available from: doi:10.3762/bjoc.21.154

Publication language
English (en)
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