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

Scheme 67. Synthesis of N-Annulated Perylene Diimide Dimers.

Scheme 67

Reagents and conditions: (a)119 PPh3, DMF, 150 °C, 21 h, 67%; (b) n-hexyl bromide, K2CO3, DMF, 120 °C, 18 h, 89–96% for 67.2a–b; (c) Br2, DCM, rt, 2 h, 94–98%; (d) Pd(dba)2, Zn dust, DMF, 100 °C, 3.5 h, 79–81%; (e)120 Br2 (neat), rt, 1 h, 93%, then Pd(dba)2, Zn dust, DMF, 120 °C, 30 min, 56%; (f) Boc2O, DMAP, K2CO3, DMF, 80 °C, 24 h, 97%; (g) 200 °C, 1 h, quant. or 180 °C in thin films; (h)121 hexabutylditin, SiliaCat DPP-Pd, toluene, 100 °C, 1 h, 63%; (i) Zn dust, Pd2(dba)3, DMF, 100 °C, 2.5 h, 66%; (j) 67.6, Pd(PPh3)4, toluene, 180 °C, microwave, 10 min, 45%.