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

Scheme 317. Synthesis of Diarylamine-Fused Porphyrins.

Scheme 317

Reagents and conditions: (a)594 DDQ (10 equiv), Sc(OTf)3 (10 equiv), ClCH2CH2Cl/MeNO2 70 °C, 1 h; (b) DDQ (10 equiv), FeCl3 (10 equiv), DCM/MeNO2, rt; (c) (1) FeCl3 (10 equiv), DCM/MeNO2, 70 °C, 1 h, (2) HCOOH, NEt3, Pd2(dba)3, SPhos, toluene, 120 °C, 1 h; (d) TFA/conc. H2SO4; (e) Zn(OAc)2·2H2O, DCM; (f) (1) p-tolylmagnesium bromide, toluene, (2) 3 M HClaq; (g) BAHA (1.1 equiv), DCM, rt, 10 min; (h) 2-chloro-1,3-bis(methoxycarbonyl)guanidine (2.2 equiv), CHCl3, 0 °C (10 min) to rt, 2.5 h for 317.7a and 7 h for 317.7a; (i) BAHA (1.1 equiv), DCM, rt, 10 min for 317.7a and 5 min for 317.7a.