Efficient Two‐Step Synthesis of Face‐to‐Face meso‐Substituted Bis(corrole) Dyads

Abstract

The synthesis of face-to-face meso-substituted bis(corrole) systems was revisited. By using a new synthetic pathway, the reaction was generalized to any type of linker and the yield was considerably increased. The dyads were obtained in yields up to 20 % from a dialdehyde linker and dipyrromethane in a one-step reaction. The best reaction conditions required a decreased amount of TFA catalyst (1.4 equiv.) and

Synthesis of Corroles and Their Heteroanalogs

“…Further optimization of this protocol stands on the modification of the ratio of substrates (8-fold excess of dipyrrane) and lowered acid loading (to 1.4 equiv), which resulted in significant improvement of the reaction outcome, i.e., 20% yield of desired product 50 …”

“…Further optimization of this protocol stands on the modification of the ratio of substrates (8-fold excess of dipyrrane) and lowered acid loading (to 1.4 equiv), which resulted in significant improvement of the reaction outcome, i.e., 20% yield of desired product 50. 87 Recently, corroles bearing the hangman scaffold drew considerable attention due to their potential application in the activation of small molecules through proton-coupled electron transfer (PCET). Their first efficient synthesis was reported by Dogutan et al in 2011.…”

Oxo(corrolato)vanadium(iv) catalyzed epoxidation: oxo(peroxo)(corrolato)vanadium(v) is the true catalytic species

“…[30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49] Corrole has excellent chelating properties; many metal complexes across the periodic table bearing corrole ligand functionalities have already been reported in the literature. [50][51][52][53][54][55][56][57][58][59][60][61][62][63] Licoccia et al first synthesized oxo(corrolato)vanadium(IV) complexes bearing b-substitution at the corrole periphery. 64 Interestingly, to date, there is no report on the oxo(corrolato)vanadium(IV) complexes bearing meso-substitution at the corrole periphery.…”

Electrochemistry and Spectroelectrochemistry of Bismanganese Porphyrin-Corrole Dyads

“…MS (MALDI-TOF): 2-[(Manganese-5,15-dimesitylcorrol-10-yl)-2 0 -(acetatomanganese-13,17-diethyl-2,3,7,8,12,18-hexamethylporphyrin-5-yl)]-diphenylether (PMes 2 COx)Mn 2 (OAc) (6OAc). This compound was prepared in 75% yield (42 mg, 0.031 mmol), as described for (PMes 2 CO)Mn 2 (OAc), starting from (PMes 2 COx)H 5 (50 mg, 0.040 mmol, 1 equiv) and Mn(OAc) 2 (40 Dyads 3-6 were quantitatively obtained by washing the corresponding dichloromethane solution of the above acetate containing derivatives with a 1 M hydrochloric acid solution. MALDI-TOF analysis of the compounds gave [M -Cl] þ as the unique ion of the spectrum.…”

“…Dyad 3. UV-vis (CH 2 Cl 2 ), λ max (nm) (ε Â 10 -3 , mol -1 L cm -1 ): 364 (67), 402 (45), 420 (40), 472 (31), 561 (11), 646 (6), 772 (2). Dyad 4.…”