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General Procedure A: Coupling of Aryl Halides with Amines A flask was charged with FeCl3 (16 mg, 0.1 mmol, CuO (8 mg, 0.1 mmol, Cs2CO3 (651 mg, 2 mmol, BINOL (57 mg, 0.2 mmol, and any remaining solids (amine and/or aryl halide, The flask was evacuated and backfilled with nitrogen (this procedure was repeated five times, Aryl halide (1 mmol, if liquid, amine (1.2 mmol, if liquid, and DMF (2 mL) were added to the flask under nitrogen atmosphere. The mixture was allowed to stir under nitrogen atmosphere at the shown temperature for the indicated period of time in the text (see Tables 1 and 2, After cooling to r.t, the mixture was diluted with CH2Cl2 (ca. 20 mL, the solution was filtered, and the filter cake was further washed with CH2Cl2 (ca. 5 mL, The filtrate was washed with 1 M NaOH (ca. 10 mL, The combined aqueous phase was extracted with CH2Cl2 2 x 10 mL, Organic l
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+].
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54149091941
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General Procedure B: Coupling of Aryl Halides with Phenols A flask was charged with FeCl3 (16 mg, 0.1 mmol, CuO (8 mg, 0.1 mmol, Cs2CO3 (651 mg, 2 mmol, 1,1′-binaphthyl-2,2′- diol (57 mg, 0.2 mmol, and any remaining solids (phenol and/or aryl halide, The flask was evacuated and backfilled with nitrogen (this procedure was repeated five times, Aryl halide (1 mmol, if liquid, phenol (1.2 mmol, if liquid, and DMF (2 mL) were added to the flask under nitrogen atmosphere. The flask mixture was allowed to stir under nitrogen atmosphere at the shown temperature for the indicated period of time in the text (see Table 3, After cooling to r.t, the mixture was diluted with CH2Cl2 (ca. 20 mL, the solution was filtered, and the filter cake was further washed with CH2Cl2 ca. 5 mL, The solvent of the filtrate was removed with the aid of a rotary evaporator, and the residue was purified by colu
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