General synthesis of meso-amidoporphyrins via palladium-catalyzed amidation.
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]
Gao
Guang-Yao
GY
Department of Chemistry, University of Tennessee, Knoxville, TN 37996-1600, USA.
Chen
Ying
Y
Zhang
X Peter
XP
D000577:Amides / Q000737:chemistry*; D001966:Bromine / Q000737:chemistry; D002384:Catalysis; D008024:Ligands; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry*
D000577:Amides; D008024:Ligands; D011166:Porphyrins; D010165:Palladium; D001966:Bromine