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THF: An Efficient Electron Donor in Continuous Flow Radical Cyclization Photocatalyzed by Graphitic Carbon Nitride
Author(s) -
Woźnica Magdalena,
Chaoui Nicolas,
Taabache Soraya,
Blechert Siegfried
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404440
Subject(s) - graphitic carbon nitride , photocatalysis , substrate (aquarium) , chemistry , carbon nitride , catalysis , continuous flow , cyclopentanes , photochemistry , mesoporous material , carbon fibers , electron donor , organic chemistry , materials science , oceanography , physics , composite number , mechanics , composite material , geology
Mesoporous graphitic carbon nitride (mpg‐C 3 N 4 ) was found to be an efficient heterogeneous photocatalyst for the metal‐free radical cyclization of 2‐bromo‐1,3‐dicarbonyl compounds. Reactions leading to functionalized cyclopentanes proceed under mild conditions and can be conducted in a continuous flow photoreactor. Compared to the batch reaction, the use of a continuous flow reactor resulted in a significant reduction in reaction time (complete conversion of 0.04 mmol of substrate in a batch was achieved after 4 h, whereas in a flow reactor the same amount of substrate was fully converted into a product within 40 min). Mechanistic studies of the reaction showed that THF plays not only the role of solvent, but is also a crucial hydrogen and electron donor.