A photolabile protection strategy for terminal alkynes
Artikel i vetenskaplig tidskrift, 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.
diels-alder reactions
substitution
o-Nitrobenzyl
p-hydroxyphenacyl
phototrigger
v364
derivatives
photolysis
dor spa
propargylic alcohols
surfaces
Terminal alkynes
nature
1993
Photolabile protection
click chemistry
p555
reaction-mechanisms
Författare
Tina Gschneidtner
Chalmers, Kemi- och bioteknik, Polymerteknologi
Kasper Moth-Poulsen
Chalmers, Kemi- och bioteknik, Polymerteknologi
Tetrahedron Letters
0040-4039 (ISSN)
Vol. 54 40 5426-5429Styrkeområden
Materialvetenskap
Ämneskategorier
Organisk kemi
DOI
10.1016/j.tetlet.2013.07.144