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Supplementary data
5203; (b) Renger, B. Synthesis 1985, 856; (c) Yamada, K.; Kubo, T.; Tokuyama, H.;
Fukuyama, T. Synlett 2002, 231.
Supplementary data (General experimental and accompanying
spectropscopic data for the compounds) associated with this arti-
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References and notes
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7. General procedure: Into a reaction tube were placed cesium fluoride (380 mg,
2.50 mmol), copper(I) iodide (10 mg, 0.05 mmol), aryl halide (1.0 mmol), amide
or heterocycle (1.2 mmol), and N,N0-dimethylethylene diamine or 8-
hydroxyquinoline (0.1 mmol). The tube was sealed, evacuated, and back-
filled with nitrogen 2–3 times, and then the vessel was charged with 2.0 mL of
solvent. The vessel was evacuated and back-filled with nitrogen twice more,
then allowed to stir at the requisite temperature (generally room temperature)
until completion. The reaction mixture was diluted with EtOAc (2 mL) and the
reaction was quenched with saturated ammonium chloride (2 mL). The
aqueous layer was removed and 3 ꢀ 2 mL EtOAc was extracted. The
combined organics were washed with brine, then dried over magnesium
sulfate, filtered, and concentrated. The crude product was purified by flash
´
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chromatography on an Isco CombiFlash purification system with
a 12 g
RediSepÒ flash cartridge using an EtOAc/hexanes gradient (0–100%, 10–
12 min).
8. When this substrate was subjected to copper-catalyzed conditions in the
presence of K3PO4, we obtained
a lower yield (59%) and lower ee (84%).
Employing Pd and Xantphos, the yield (20%)as well as ee (59%) was lower.