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In summary, we have established a facile and efficient
synthesis of 9-azajulolidine in reasonable yield from
readily available reagents. Because of its highly elec-
tron-rich character, 9-azajulolidine is an effective auxil-
iary ligand for promoting post-Ullmann coupling
reactions18 leading to the construction of C(aryl)–het-
eroatom (N, O, S) bonds.
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Acknowledgment
This study was supported by the National Science
Council and Ministry of Economic Affairs (95-EC-17-
A-08-S1-042) of Taiwan.
Supplementary data
Detailed experimental procedures, spectroscopic charac-
terization, and NMR spectra of new compounds are
available. Supplementary data associated with this arti-
12. Canibano, V.; Rodriguez, J. F.; Santos, M.; Sanz-Tejedor,
A.; Carreno, M. C.; Gonzalez, G.; Garcia-Ruano, J. L.
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18. General experimental procedure: CuI (9.5 mg, 0.05 mmol,
5 mol %), base (2.0 mmol), aryl iodide (1 mmol), and aryl
amine (1.2 mmol) were added to
a two-neck flask
equipped with a septum. The flask was evacuated and
back filled with Ar. Toluene (4 mL), and 9-AJ (0.1 M in
toluene, 1 mL, 0.1 mol) was added via a syringe at room
temperature. The reaction mixture was heated at 110 °C
for 40 h and then cooled to room temperature. Water
(20 mL) was added and the mixture extracted with CH2Cl2
(40 mL). The combined organic phases were dried
(MgSO4) and the solvent evaporated in vacuo to yield
the crude product, which was purified through silica gel
chromatography.
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