Photochemical Formation of Dibenzosilacyclohept-4-yne for Cu-Free Click Chemistry with Azides and 1,2,4,5-Tetrazines

Investor logo
Investor logo

Warning

This publication doesn't include Faculty of Arts. It includes Faculty of Science. Official publication website can be found on muni.cz.
Authors

MARTÍNEK Marek FILIPOVÁ Lenka GALETA Juraj LUDVÍKOVÁ Lucie KLÁN Petr

Year of publication 2016
Type Article in Periodical
Magazine / Source Organic Letters
MU Faculty or unit

Faculty of Science

Citation
Web http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b02367
Doi http://dx.doi.org/10.1021/acs.orglett.6b02367
Field Organic chemistry
Keywords DIELS-ALDER REACTIONS; CYCLOADDITION REACTIONS; BIOORTHOGONAL REACTIONS; LIVING CELLS; GENERATION; REACTIVITY; SIEBENRINGSYSTEMEN; BIOCONJUGATION; CYCLOHEPTYNES; BIOMOLECULES
Description Photochemical generation of dibeniOsilacyclohept-4-yne 3 from the corresponding, cydopropenone 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 (Phi = 0.58-0.71) photoreleased from 1 and undergoes remarkably fast, selective, and high-yielding 1,3-dipolar cycloaddition with benzyl azide (similar to 20 M-1 s(-1)) or [4 + 2] inverse electron-demand Diels Alder reaction with 1,2,4,5-tetrazines (similar to 260 M-1 s(-1)) in both methanol and acetonitrile.
Related projects:

You are running an old browser version. We recommend updating your browser to its latest version.