Release of Terminal Alkynes via Tandem Photodeprotection and Decarboxylation of o -Nitrobenzyl Arylpropiolates in a Flow Microchannel Reactor
Artikel i vetenskaplig tidskrift, 2018

Photocleavable protecting groups (PPGs) offer a complementary protection paradigm compared to traditional protection groups. Herein, an o-nitrobenzyl (NB) PPG was employed to protect a variety of arylpropiolic acids. Upon a cascade of light-triggered photodeprotection in a microchannel reactor (residence times of 100-500 s), followed by Cu-catalyzed decarboxylation at 60 °C, the NB-protected arylpropiolic acid afforded a terminal alkyne. This terminal alkyne was further reacted in situ with an azide via click chemistry to yield a 1,2,3-triazole in a one-pot reaction. Furthermore, the effect of different substituents (methyl, vinyl, allyl, and phenyl) at the benzylic position on the rate of photodeprotection was studied. The quantum yields of photolysis for the benzylic-substituted esters were determined to be as high as 0.45 compared to the unsubstituted ester with a 0.08 quantum yield of photolysis.

Författare

Behabitu Ergette Tebikachew

Chalmers, Kemi och kemiteknik, Tillämpad kemi, Polymerteknologi

Karl Börjesson

Göteborgs universitet

Nina Kann

Chalmers, Kemi och kemiteknik, Kemi och biokemi, Fysikalisk kemi

Kasper Moth-Poulsen

Kasper Moth-Poulsen Group

Bioconjugate Chemistry

1043-1802 (ISSN) 1520-4812 (eISSN)

Vol. 29 4 1178-1185

Ämneskategorier

Kemiska processer

Biokatalys och enzymteknik

Organisk kemi

DOI

10.1021/acs.bioconjchem.7b00812