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Exploiting Photochemical Processes in Multi‐Step Continuous Flow: Derivatization of the Natural Product Clausine C
Author(s) -
ParisienCollette Shawn,
Collins Shawn K.
Publication year - 2018
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201800096
Subject(s) - derivatization , yield (engineering) , continuous flow , chemistry , flow chemistry , natural product , catalysis , combinatorial chemistry , photochemistry , organic chemistry , materials science , high performance liquid chromatography , biochemical engineering , engineering , metallurgy
The synthesis and derivatization of carbazoles based upon the natural product clausine C has been accomplished using two different two‐step continuous processes. The resulting carbazoles (9 examples, 33–74 % yield) were prepared by means of a continuous flow set‐up integrating a UV‐mediated transformation employing a purple LED reactor ( λ =394 nm) as the first step in the multi‐step sequence. The second derivatization step involved cross‐coupling through Pd‐catalyzed Suzuki cross‐coupling or Ni‐catalyzed metallophotoredox cross‐coupling with potassium trifluoroborate salts. The latter represents the first example of using sequential photochemical reactors, at different wavelengths, in a continuous flow process.