Fig. 5: Scale up experiment for 3a and its synthetic transformations. | Nature Communications

Fig. 5: Scale up experiment for 3a and its synthetic transformations.

From: Desymmetric homologating annulation to access chiral pentafulvenes and their application in bioimaging

Fig. 5

a 3a (0.1 mmol, 1 equiv.), 3,5-bis(trifluoromethyl)phenyl isocyanate (0.1 mmol, 1 equiv.), DCM (1 mL), rt, 8 h. b 3a (0.1 mmol, 1 equiv.), 3,5- bis(trifluoromethyl)benzoyl chloride (0.12 mmol, 1.2 equiv.), DCM (1 mL), rt, 12 h. c 3a (0.1 mmol 1 equiv.), NaNO2, 0.15, 48 % HBr 250 µL, −50 °C 1 h, then add 2 mL of Et2O, −8 °C for 2 h, again cooled to −40 °C, 100 mg Na2CO3, stirred overnight. d 3a (0.1 mmol, 1 equiv.) in toluene 1 mL, heated at 180 °C, 16 h. e 3a (0.1 mmol, 1 equiv., NBS (0.5 mmol, 5 equiv.). DMF, rt, 1 min.

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