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2 when reacted with aryl halides beating substituents at the ortho-position.
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3, and 1.5 mL of anhydrous toluene at room temperature. The resulting solution was stirred for 30 min at room temperature before being heated at 110°C. After 1 h, the reaction mixture was cooled, concentrated in vacuo, and chromatographed (hexanes/EtOAc = 9/1) to afford 41 mg of 3h in 91% yield.
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0141559480
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note
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2 (3 mL) were added pyridine (0.8 mL; 0.094 mmol; 1.2 equiv) and NBS (17 mg; 0.094 mmol; 1.2 equiv) at room temperature. The reaction mixture was stirred for 2 h at room temperature, concentrated in vacuo, and purified by column chromatography (hexanes/EtOAc = 10/1) to afford 18 mg of the azobenzene 5b in 84% yield.
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36
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0141670881
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note
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We isolated brominated N-Boc diaryl hydrazine (Br ortho to the OMe group) as a byproduct in 20% yield.
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