ACS Catalysis
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In summary, a novel palladium-catalyzed carbonylation
of indoles with CO and aromatic boronic acids for the
synthesis of indol-3-yl aryl ketones has been developed.
The reaction employs readily available indoles and aro-
matic boronic acids as the substrates and tolerates a wide
range of functional groups. A series of valuable indol-3-yl
aryl ketones were easily synthesized in high yields under
mild conditions. Further scope of the reaction is under-
way.
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EXPERIMENTAL SECTION
General Procedure for Carbonylation of Indoles with
Arylboronic Acids: Indoles 1 (0.2 mmol), aryboronic acids 2
(0.24 mmol), Pd(OAc)2 (5 mol%, 2.2 mg), I2 (2.4 mmol, 60
mg), KOH (0.6 mmol, 33.6 mg), pyridine (0.2 mmol, 15.8 mg),
CsF (0.3 mmol, 45 mg), and toluene (3 mL) was charged in a
10 mL round bottom flask. Then, the flask was evacuated and
back-filled with CO (3-times, balloon) and stirred under CO
(balloon) at 80 oC for 12 h. When the reaction was completed
(detected by TLC), the mixture was cooled to room tempera-
ture and carefully vented to discharge the excess CO. The
reaction was quenched with H2O (10 mL) and extracted with
EtOAc (3 × 10 mL). The combined organic layers were dried
over anhydrous Na2SO4 and then evaporated in vacuo. The
residue was purified by column chromatography on silica gel
to afford the corresponding indol-3-yl aryl ketones 3 with
hexanes/ethyl acetate (5:1 to 3:1) as the eluent.
ASSOCIATED CONTENT
Supporting Information
Detailed experimental procedures, characterization data and
copies of NMR spectra for all products. This material is avail-
AUTHOR INFORMATION
Corresponding Author
*E-mail: guanzhh@nwu.edu.cn.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENT
This work was supported by generous grants from the Na-
tional Natural Science Foundation of China (21472147,
21272183), and the Fund of the Rising Stars of Shanxi Province
(2012KJXX-26).
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