Bromine–lithium exchange as a straightforward method to obtain meso-tetrakis(4-formylphenyl)porphyrin: a versatile intermediate. Issue 37 (9th September 2015)

• Record Type: Journal Article
• Authors: Önal, Emel; Ahsen, Vefa; Pécaut, Jacques; Luneau, Dominique; Hirel, Catherine
• Is Part Of: Tetrahedron letters. Volume 56:Issue 37(2015)
• Page Start: 5157
• Page End: 5160
• Publication Date: 2015-09-09
• Subjects: Porphyrin -- Bromine–lithium exchange -- Bouveault reaction -- Formyl group; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.07.021
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: A three step, one-pot reaction has been developed for the introduction of the formyl functional group to the meso 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.