A photolabile protection strategy for terminal alkynes
Journal article, 2013
We present a strategy for photolabile protection of terminal alkynes. Several photo-caged alcohols were synthesized via mild copper(II)-catalyzed substitution between tertiary propargylic alcohols and 2-nitrobenzyl alcohol to build up robust, base stable o-nitrobenzyl (NB) photo-cleavable compounds. We compare the new photolabile protecting group with the commonly used alkyne protecting group, 2-methyl-3-butyn-2-ol and the results show that NB ethers are stable under the cleaving conditions for the cleavage of methylbutynol protected alkynes. Additionally, we present the synthesis of photo-cleavable NB derivatives containing thiol groups that can serve as agents for photoinduced surface functionalization reactions.
nature
v364
Photolabile protection
derivatives
p-hydroxyphenacyl
click chemistry
1993
diels-alder reactions
reaction-mechanisms
Terminal alkynes
propargylic alcohols
substitution
photolysis
phototrigger
dor spa
p555
surfaces
o-Nitrobenzyl
Author
Tina Gschneidtner
Chalmers, Chemical and Biological Engineering, Polymer Technology
Kasper Moth-Poulsen
Chalmers, Chemical and Biological Engineering, Polymer Technology
Tetrahedron Letters
0040-4039 (ISSN) 18733581 (eISSN)
Vol. 54 40 5426-5429Areas of Advance
Materials Science
Subject Categories
Organic Chemistry
DOI
10.1016/j.tetlet.2013.07.144