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and terminal alkynes was developed. The reactions were carried
out successively in DMSO at 80 °C to provide the corresponding
2-substituted benzo[b]furans in good to excellent yields with a
great diversity. Further investigation on the application of this
strategy is currently underway in our lab.
Acknowledgment
This work was supported by National Natural Science
Foundation of China (Grants 21302126).
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10. The experimental procedures and characterization data for compound
3a. A sealable reaction tube equipped with a magnetic stirrer bar was charged
with 2-iodophenol 1a (1 mmol), phenylacetylene 2a (1 mmol), NaOH (2
mmol), CuI (0.1 mmol), Proline (0.3 mmol) and DMSO (5 mL), the reaction
vessel was placed in an oil bath at 80 oC under N2 . After stirring the mixture
at this temperature for 12 h, it was cooled to room temperature and diluted
with ethyl acetate, washed with water and brine, dried over by MgSO4. After
the solvent was removed under reduced pressure, the residue was purified by
column chromatography on silica gel to afford 3a (171 mg, 88 %) as a
colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.87 (d, J = 8.3 Hz, 2H), 7.58 (d,
J = 7.5 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 7.44 (t, J = 7.6 Hz, 2H), 7.35 (d, J =
7.3 Hz, 1H), 7.32-7.27 (m, 1H), 7.25 (d, J = 7.5 Hz, 1H), 7.00 (s, 1H). 13
C
NMR (125 MHz, CDCl3) δ 156.04, 155.03, 130.61, 129.35, 128.86, 128.61,
125.04, 124.35, 123.03, 121.00, 111.26, 101.41. ESI-MS m/z: 195.2(M+1)+.
HRMS calcd for C14H10NaO (M+Na) + requires 217.0629, found 217.0635.
1. A one-pot synthetic process of 2-substituted
benzo[b]furan/hetero-benzo[b]furan
2. Starting from 2-iodo-phenol and 1-alkynes
3. Catalyzed by CuI/proline in mild condition,
Palladium and Phosphorus free.
Graphical Abstract