%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