Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines
Status PubMed-not-MEDLINE Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
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.
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