Organic Letters 2004-05-27

General synthesis of meso-amidoporphyrins via palladium-catalyzed amidation.

Guang-Yao Gao, Ying Chen, X Peter Zhang

Index: Org. Lett. 6 , 1837, (2004)

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Abstract

A series of meso-amidoporphyrins were facilely synthesized by direct reactions of meso-brominated porphyrins with amides via palladium-catalyzed amidation reaction. Using a combination of palladium precursor Pd(OAc)(2) or Pd(2)(dba)(3) and phosphine ligand Xantphos, both 5-bromo-10,20-diphenylporphyrin and 5,15-dibromo-10,20-diphenylporphyrin, as well as their zinc complexes, can be effectively coupled with a wide variety of amides to give the corresponding mono- and bis-substituted meso-amidoporphyrins in high yields under mild conditions. [reaction: see text]