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.

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

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)

Vol. 54 40 5426-5429

Areas of Advance

Materials Science

Subject Categories

Organic Chemistry

DOI

10.1016/j.tetlet.2013.07.144

More information

Latest update

5/17/2018