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Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines
journal contribution
posted on 2016-09-13, 21:31 authored by Marek Martínek, Lenka Filipová, Juraj Galeta, Lucie Ludvíková, Petr KlánPhotochemical
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.
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AzidegenerationTetrazineCu-Free Click ChemistryDibenzosilacyclohept -4-yneinverse-electron-demanddibenzosilacyclohept -4-yne 3copper-free click reactionsmethanolazideabsorption spectroscopy studiesDieldipolaracetonitrileSteady-state irradiationcycloadditionbenzylphotoreleasedalkyne 3tetrazinecyclopropenone 1Photochemical Formation
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