Palladium-Catalyzed Sequential Reactions via Allene Intermediates
COMMUNICATIONS
À
F. M. Sabbatini, G. Tarzia, M. E. Tranquillini, Bioorg.
Med. Chem. Lett. 2003, 13, 2113; g) G. Trippeꢀ, F. L.
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Clercq, J. Balzarini, J. Bermejo, F. Esterez, R. Romag-
nodi, J. Med. Chem. 2004, 47, 2877.
pyrrole derivatives. The reaction features one C C
bond and two C N bonds formed to construct the
À
pyrrole unit and two rings efficiently assembled in
one stroke. Further efforts to explore the reaction
scope as well as the mechanism study are currently
underway.
[3] a) D. Black, 1H-Pyrroles, in: Hetarenes and Related
Ring Systems: Science of Synthesis, (Ed.: G. Maas),
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[4] For some recent examples on the synthesis of pyrroles,
see: a) M. Blangetti, A. Deagostino, C. Prandi, S. Ta-
basso, P. Venturello, Org. Lett. 2009, 11, 3914; b) E.
Merkui, C. Boersch, W. Frank, T. J. J. Mꢃller, Org. Lett.
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Experimental Section
General Procedure
An oven-dried Schlenk tube containing a Teflon-coated stir
bar was charged with PdACTHNUTRGEN(UNG Ph3P)2Cl2 (9 mg, 5 mol%), CuI
(1.5 mg, 3 mol%) and 1 (0.25 mmol). The Schlenk tube was
sealed and then evacuated and backfilled with N2 (3 cycles).
A solution of 2 (0.3 mmol) in 3 mL of toluene or THF and
1 mL of Et3N was subsequently injected to the Schlenk tube.
The reaction mixture was stirred at room temperature or
608C. After the reaction was completed (monitored by
TLC), the reaction mixture was quenched with dilute HCl
and extracted with Et2O (3ꢂ15 mL). The combined organic
layers were dried over anhydrous Na2SO4. After filtration
and removal of the solvent under vacuum, the residues were
purified with flash chromatography (silica/petroleum ether-
ethyl acetate 6:1 to 2:1 v/v) to afford 3.
´
72, 3941; h) R. Martin, M. Rodnguez Rivero, S. L.
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Acknowledgements
We are grateful to the National Natural Science Foundation
of China (Project Nos. 20732005 and 20872127) and National
Basic Research Program of China (973 Program,
2009CB825300) for financial support.
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