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

Scheme 316. Synthesis of meso-Pyrrole Porphyrins.

Scheme 316

Reagents and conditions: (a)593 (1) DCM, TFA, p-tolualdehyde, rt, 16 h, (2) DDQ (2 equiv); (b) EtONa (10 equiv), Ph3P+CH2PhCl or Et4N+Cl (10 equiv), EtOH, then addition of 316.2a or 316.2b, 24 h; (c) (1) TFA (10%) followed by neutralization with Et3N, (2) Ni(OAc)2, DMF, reflux, 1 h; (d) TFA/H2SO4 neutralization with Na2CO3, 2 h; (e) CHCl3/MeOH, Zn(OAc)2, 1 h; (e) THF, nBu4N+F, N2.