Abstract
An iron-catalyzed procedure was employed to achieve both the Sonogashira cross-coupling and intramolecular o-arylation of o-iodophenols and aryl acetylenes/1-substituted-2-trimethylsilyl acetylenes. A variety of 2-arylbenzo[b]furans were synthesized in moderate to good yields under the catalysis of 5% FeCl3 and 10% 1,10-phenanthroline.
GRAPHICAL ABSTRACT
ACKNOWLEDGMENTS
This work was financially supported by the Natural Science Foundation of China (No. 21272169), the Specialized Research Fund for the Doctoral Program Foundation of Higher Education of China (No. 2060335036), and Natural Science Foundation of Zhejiang Province for founding (No. Y406049).
Notes
a Reaction conditions: FeCl3 (0.025 mmol), ligand (0.05 mmol), o-iodophenol (0.5 mmol), phenylacetylene (0.75 mmol), and base (2.0 mmol) in solvent (2.0 mL) under N2.
b Isolated yield.
c Fe2O3 (0.025 mmol) was used.
d No FeCl3 was used.
a Reaction conditions: FeCl3 (0.025 mmol), 1,10-phenanthroline (0.05 mmol), o-iodophenols (0.5 mmol), phenylacetylene (0.75 mmol), and Cs2CO3 (2.0 mmol) in xylene (2.0 mL) under N2.
b Isolated yield.
a Reaction conditions: FeCl3 (0.025 mmol), 1,10-phenanthroline (0.05 mmol), o-iodophenols (0.5 mmol), 1-substituted-2-trimethylsilyl acetylene (0.75 mmol), and Cs2CO3 (2.0 mmol) in xylene (2.0 mL) under N2.
b Isolated yield.