Bromine-lithium exchange as a straightforward method to obtain meso-tetrakis(4-formylphenyl)porphyrin: a versatile intermediate

Emel Oenal (1, 2) , Vefa Ahsen (2) , Jacques Pecaut (3) , Dominique Luneau (1) , Catherine Hirel (2)

1 LMI - Laboratoire des Multimatériaux et Interfaces
2 Department of chemistry - Gebze Technical University
3 SCIB - UMR E3 - Service de Chimie Inorganique et Biologique

A three step, one-pot reaction has been developed for the introduction of the formyl functional group to the mesa position of porphyrins. Symmetric meso-tetrakis(4-formylphenyl)porphyrin ((CHO)(4)TPPH2), an important cornerstone in porphyrin chemistry, was obtained selectively in good yields via bromine-lithium exchange and subsequent Bouveault reaction. The meso-tetrakis(4-formylphenyl)porphyrin was fully characterized by HR-ESI, UV-vis, NMR, and single crystal X-ray diffraction. (C) 2015 Elsevier Ltd. All rights reserved.

Keywords: Porphyrin; Bromine-lithium exchange; Bouveault reaction; Formyl group; Sensitized Solar-Cells

Domains: Physics [physics]

Emel Oenal, Vefa Ahsen, Jacques Pecaut, Dominique Luneau, Catherine Hirel. Bromine-lithium exchange as a straightforward method to obtain meso-tetrakis(4-formylphenyl)porphyrin: a versatile intermediate. Tetrahedron Letters, 2015, 56 (37), pp.5157-5160. ⟨10.1016/j.tetlet.2015.07.021⟩. ⟨cea-01734600⟩