Fig. 3: Application of mild and base-free conditions in the functionalization of substrates prone to decomposition and racemization.
From: Nickel catalyzed C-N coupling of haloarenes with B2N4 reagents
A Enantioretention experiment. B Base-sensitive coupling partners. C Synthesis of base-sensitive AD PET tracer analog. Condition A: 2-amino-6-fluorobenzothiazole (1.0 equiv.), ethylene glycol (4 equiv.), KOH (6.0 M, 30 equiv.), reflux at 140 °C for 24 h; condition B: bis(2-amino-5-fluorophenyl)disulfide (1.0 equiv.), 4-bromobenzaldehyde (1.02 equiv.), sodium metabisulfite (1.02 equiv.), DMSO (0.17 M), reaction at 120 °C for 2 h; condition C: 2-(4-Bromophenyl)−6-fluorobenzothiazole (0.2 mmol), B2(NMe2)4 (0.2 mmol), Ni(acac)2 (10 mol%), DMF (0.5 mL), reaction for 24 h under 80 °C. AD Alzheimer’s disease, PET the positron emission computed tomography. See SI for full experimental details and conditions.
