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

Scheme 336. Synthesis of Asymmetric Carbazole-Based Porphyrins and Their Oligomers.

Scheme 336

Reagents and conditions: (a)631 (1) 336.2a or 336.2b, p-TSA (0.2 equiv), DCM, rt, dark, 1 h, (2) DDQ (1 equiv), 10 min; (b)631 (1) 336.2c, CF3COOH (1 equiv), DCM, rt, dark, 90 min, (2) DDQ (2 equiv), 10 min; (c)630 (1) Pd2(dba)3, SPhos, CsF, Cs2CO3, reflux, 48 h, (2) MnO2; (d)630 NBS (0.9 equiv), CHCl3; (e)630 NBS (3.7 equiv), CHCl3; (f)630 (Bpin)2 (2.9 equiv), Pd(dppf)Cl2, KOAc, 1,4-dioxane, reflux; (g)630 (Bpin)2 (9.8 equiv), Pd(dppf)Cl2, KOAc, 1,4-dioxane, reflux; (h)630336.6a/336.7a (1:1), Pd2(dba)3, PPh3, CsF, Cs2CO3, toluene/DMF, reflux, 48 h; (i)630336.6a/336.7b (1:0.5), Pd2(dba)3, PPh3, CsF, Cs2CO3, toluene/DMF, reflux, 48 h.