La(OTf)3-Catalyzed Synthesis of Nickel(II) β-Iminoporphyrins and Their Conversion to β-Substituted Porphyrin-Thiazolidinone Hybrids

Abstract

Two diverse series of nickel(II) β-iminoporphyrins were prepared in good yields by the reaction of corresponding 2-formyl-and 2-amino-5,10,15,20-tetraphenylporphyrins with primary amines and aldehydes, respectively, in toluene containing a catalytic amount of La(OTf)3 under reflux conditions. These 2-iminoporphyrins further served as precursors to construct novel nickel(II) complexes of β-substituted porphyrinic thiazolidinones in moderate yields on reaction with mercaptoacetic acid in refluxing toluene. All the synthesized porphyrins have been characterized on the basis of spectral data analysis.

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

“…Continuing our work on the functionalization of porphyrin at the meso -position [ 32 – 33 ], we used the CuAAC click protocol to synthesize meso -phenyltriazole-linked porphyrin-coumarin dyads 44–48 in good to excellent yields. Firstly, Zn(II) meso -phenyltriazole-linked porphyrin-coumarin conjugates 44a–48a were synthesized by using the “click reaction” between zinc(II) 5-(4-azidophenyl)-10,15,20-triphenylporphyrin ( 39a ) and diverse alkyne-substituted coumarins 6–10 in DMF containing CuSO 4 ·5H 2 O and ascorbic acid at 80 °C [ 34 ] ( Scheme 8 ).…”