10.1002/chem.201706067
Chemistry - A European Journal
FULL PAPER
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In summary, we have developed a one-step method for the
direct synthesis of a variety of polycyclic furo[3,4-b]indol-1-ones
[4]
via
carbonylation and lactonization process from suitably
functionalized 2-alkynylanilines. This methodology is
a
novel palladium-catalyzed sequential indolization,
operationally very simple and leads to furo[3,4-b]indol-1-ones in
fair to high yields using molecular oxygen as the sole oxidant.
The described methodology demonstrates once again the
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Experimental Section
General procedure for the PdI2/KI-catalyzed synthesis of 2: A 45 mL
stainless steel autoclave was charged with substrate 1 (1 mmol), PdI2
(3.6 mg, 1 mol%), KI (16 mg, 10 mol%) and dry MeCN (4 mL). The
autoclave was sealed and pressurized with CO (12 bar) and air (48 bar).
The reaction mixture was stirred at 120 °C for 24 h, after which the
autoclave was cooled, degassed and opened. The solvent was
evaporated, and the product
chromatography on silica gel.
2
was purified by flash column
Acknowledgements
[7]
This work was supported by the “Ministero dell’Università e della
Ricerca Scientifica e Tecnologica”. The facilities of “Centro
Interfacoltà di Misure” (University of Parma) were used for
recording NMR spectra.
The main role of the oxygen consists in the oxidation of I- to I2, which in
Keywords: Carbonylation • Cyclization • Fused Heterocycles •
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Indoles • Palladium
2-
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