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Facile and efficient synthesis of meso-arylamino- and alkylamino-substituted porphyrins via palladium-catalyzed amination.

Authors
  • Chen, Ying
  • Zhang, X Peter
Type
Published Article
Journal
The Journal of organic chemistry
Publication Date
May 30, 2003
Volume
68
Issue
11
Pages
4432–4438
Identifiers
PMID: 12762748
Source
Medline
License
Unknown

Abstract

meso-Arylamino- and alkylamino-substituted porphyrins were efficiently synthesized by reactions of meso-halogenated porphyrins with amines via palladium-catalyzed amination. The combination of palladium acetate and the commercially available phosphine ligand bis(2-diphenylphosphinophenyl) ether (DPEphos) is effective for catalyzing the couplings of both [5-bromo-10,20-diphenyl porphyrino]zinc(II) and [5,15-dibromo-10,20-diphenylporphyrino]zinc(II) with amines to give the corresponding monoamino- and diamino-substituted porphyrins in high yields under mild conditions. The corresponding halogenated free-base porphyrins also underwent the cross-coupling reactions efficiently under similar catalytic conditions.

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