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

Scheme 350. Synthesis of Porphyrin Tapes.

Scheme 350

Reagents and conditions: (a)652 (1) 350.3a, CH3SO3H (15 mol %), (2) DDQ (3 equiv), DCM, 0 °C, 2 h, then rt 15 min; (b) (1) 350.3b, p-TsOH·H2O (1 equiv), (2) DDQ (6 equiv), DCM, 0 °C, 2 h, then rt 15 min; (c) (1) H2SO4, TFA, rt, 5 days, (2) Zn(OAc)2·2H2O (60 equiv), CHCl3/MeOH, 50 °C, o/n; (d) (1) H2SO4, TFA, 0 °C, 30 min, (2) Zn(OAc)2·2H2O (60 equiv), CHCl3/MeOH, 50 °C, o/n; (e) DDQ (8 equiv), Sc(OTf)3 (8 equiv), toluene, 100 °C, 5 h; (f) DDQ (8 equiv), Sc(OTf)3 (8 equiv), toluene, 80 °C, 4 h; (g) H2SO4, TFA, 0 °C, 30 min, (2) Zn(OAc)2·2H2O (40 equiv), CHCl3/MeOH, 50 °C, o/n; (h) DDQ (5 equiv), Sc(OTf)3 (5 equiv), toluene, rt, 3 h; (i) DDQ (12 equiv), Sc(OTf)3 (12 equiv), toluene, 80 °C, 3 h.