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

Abstract

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.