Beilstein J. Org. Chem.2024,20, 1020–1028, doi:10.3762/bjoc.20.90
increase in temperature facilitates the ligand coupling between the phenyl group and the carboxylate counterion. When heated at 140 °C for 2.5 h under solvent-free conditions, iodonium salt 7aa underwent carboxylate O-phenylation with complete phenyl group transfer, resulting in the formation of phenyl
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Graphical Abstract
Scheme 1:
Synthetic approaches of diaryliodonium(III) trifluoroacetates.
Beilstein J. Org. Chem.2018,14, 345–353, doi:10.3762/bjoc.14.22
transformed into 4-phenylcoumarin derivatives bearing C–H, C–S, C–N, and C–C bonds at 3-position.
Keywords: 3-aryl-2-propynoic acid; bromo-cyclization; coumarin; diaryliodonium triflate; O-phenylation; Introduction
Coumarin is a benzo-α-pyrone and one of the typical heterocyclic compounds. The importance of
preparation of 3-bromo-4-phenylcoumarins 3a from 3-phenyl-2-propynoic acid (1a) with daryliodonium triflates B–E.
Derivatization of 3-bromo-4-phenylcoumarin.
Possible reaction pathway.
O-Phenylation of 3-phenyl-2-propynoic acid (1a) with diphenyliodonium triflate (A).
Halocyclization of phenyl 3-phenyl-2
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Graphical Abstract
Scheme 1:
One-pot preparation of 4-aryl-3-bromocoumarins 3 from 3-aryl-2-propynoic acids 1 with diphenyliodon...