Synthesis of β‐Substituted meso‐Tetraaryl‐21,23‐dithiaporphyrins by Heck Reaction

Abstract

Keywords: Synthetic methods / Porphyrinoids / Macrocycles / Electronic effects meso-Tetraphenyl-21,23-dithiaporphyrin was selectively monobrominated at one β-pyrrolic position in good yields. This dithiaporphyrin was then functionalized by Heck reaction with styrene derivatives containing different electronic

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“…CDA type reactions may occasionally occur spontaneously, as evidenced by a recent report by Cavaleiro, de Souza, Neves et al, who observed formation of 355.2 under Heck-type conditions (Scheme ). The UV–vis spectrum of 355.2 exhibited a broad and split Soret band, which was ascribed to the high deformation of the macrocycle caused by its five-membered ring.…”

“… a Reagents and conditions: (a) styrene, Pd­(OAc) 2 , K 2 CO 3 , PPh 3 , DMF/toluene (1:1, v/v), reflux, 1 h. …”

Efficient access to β-vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

“…Having this in mind and following our interest in the development of synthetic approaches to prepare novel porphyrin derivatives [28–30], we decided to explore the palladium-catalyzed cross-coupling reaction of meso -tetraphenyl-β-bromoporphyrin using N -tosylhydrazone derivatives with different electronic features for the preparation of new β-alkenyl-type porphyrin derivatives. This approach can provide interesting compounds with potential biological properties or might become important templates for further functionalization procedures (Scheme 2).…”