Selective meso-monobromination of 5,15-diarylporphyrins via organopalladium porphyrins
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The selective meso-monobromination of 5,15-diarylporphyrins is difficult to achieve and extensive chromatography is required to obtain pure products. A sequence of (i) dibromination, (ii) selective monoinsertion of Pd(dppe) (dppe = 1,2-bis(diphenylphosphino)ethane) and (iii) hydrodepalladation using methanolic base affords pure monobromoporphyrins in typically >= 60% overall yield without isolation of the organopalladium porphyrin. Monobromo derivatives of even highly lipophilic 5,15-diarylporphyrins are thus readily available without tedious, expensive and environmentally undesirable chromatography. Copyright (c) 2004 Society of Porphyrins T Phthalocyanines.
Journal of Porphyrins and Phthalocyanines