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. 2021 Dec 1;122(1):565–788. doi: 10.1021/acs.chemrev.1c00449

Scheme 31. Synthesis of Extended Perylenoids Containing a Coumarin Substructure.

Scheme 31

Reagents and conditions: (a)55 1-naphthylboronic acid, Pd(PPh3)4, K2CO3, 4:1 toluene/H2O, 90 °C, 2 h, 87%; (b) AlCl3, NaCl, 140 °C, 4 h, 38%; (c) NBS, Bz2O2, DCM, 30 °C, 12 h, 89%; (d) RB(OH)2, Pd(PPh3)2Cl2, K3PO4, 5:1 EtOH/H2O, 90 °C, 8 h, then 5:1 EtOH/H2O, air, hν (blue LED), rt, 3 h, 54–87%; (e) MeSO3H, rt, 16 h, 58%; (f) MeI, K2CO3, DMF, rt, 5 h, 85% or 1-bromopentane, Na2CO3, KI, DMF, reflux, 16 h, 48%; (g) NBS, Bz2O2, CHCl3, rt, 1 h, 82–84%.