%0 Journal Article %A Martínek, Marek %A Filipová, Lenka %A Galeta, Juraj %A Ludvíková, Lucie %A Klán, Petr %D 2016 %T Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines %U https://acs.figshare.com/articles/journal_contribution/Photochemical_Formation_of_Dibenzosilacyclohept-4-yne_for_Cu-Free_Click_Chemistry_with_Azides_and_1_2_4_5-Tetrazines/3826596 %R 10.1021/acs.orglett.6b02367.s001 %2 https://acs.figshare.com/ndownloader/files/5965830 %K Azide %K generation %K Tetrazine %K Cu-Free Click Chemistry %K Dibenzosilacyclohept -4-yne %K inverse-electron-demand %K dibenzosilacyclohept -4-yne 3 %K copper-free click reactions %K methanol %K azide %K absorption spectroscopy studies %K Diel %K dipolar %K acetonitrile %K Steady-state irradiation %K cycloaddition %K benzyl %K photoreleased %K alkyne 3 %K tetrazine %K cyclopropenone 1 %K Photochemical Formation %X Photochemical generation of dibenzosilacyclohept-4-yne 3 from the corresponding cyclopropenone 1 and its copper-free click reactions are reported. Steady-state irradiation, kinetic, and transient absorption spectroscopy studies revealed that strained alkyne 3 is rapidly (<5 ns) and efficiently (Φ = 0.58–0.71) photoreleased from 1 and undergoes remarkably fast, selective, and high-yielding 1,3-dipolar cycloaddition with benzyl azide (∼20 M–1 s–1) or [4 + 2] inverse-electron-demand Diels–Alder reaction with 1,2,4,5-tetrazines (∼260 M–1 s–1) in both methanol and acetonitrile. %I ACS Publications