New downstream synthetic route of 5,10,15,20-Tetraphenyl-21H,23H-porphine copper(II)

14172-91-9 5,10,15,20-Tetraphenyl-21H,23H-porphine copper(II) 3722750, acopper-catalyst compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14172-91-9,5,10,15,20-Tetraphenyl-21H,23H-porphine copper(II),as a common compound, the synthetic route is as follows.,14172-91-9

To a stirred solution of (meso-tetraphenylporphyrinato)copper(II) (1c; 237 mg, 0.35 mmol) inCHCl3 (530 mL) at room temperature, a solution of 25% aqueous nitric acid (freshly prepared fromfuming yellow HNO3, d = 1.52; large excess, 140 mL, 637 mmol) was added dropwise during ca5 min. The reaction mixture was intensively stirred under argon in a round-bottomed ask, protectedagainst light, for 30-40 min with TLC monitoring (CHCl3/n-hexane-1:1). Then, the mixture waspoured into aqueous solution of 5% NaHCO3 (200 mL), and shaken carefully in a separatory funnel.The separated organic layer was washed with water (4 200 mL), and dried with anhydrousMgSO4/Na2CO3. After evaporating the solvent, the residue was subjected to column chromatography(eluent: CHCl3/n-hexane1:1) to give (2-nitro-5,10,15,20-tetraphenylporphyrinato)copper(II) (2c; 71 mg, 28%) and a mixture of dinitro-substituted isomers (150 mg, 56%). Thedinitro-isomers were separated on preparative TLC (CHCl3/n-hexane-1:1, four times developed),allowing isolation of: (a) (2,7-dinitro-5,10,15,20-tetraphenylporphyrinato)copper(II) (3ca; 40 mg,15%); (b) (3,7-dinitro-5,10,15,20-tetraphenylporphyrinato)copper(II) (3cb; 35.5 mg, 13%); (c)(2,8-dinitro-5,10,15,20-tetra-phenylporphyrinato)copper(II) (3cc) contaminated with small amountsof (3,7-dinitro-5,10,15,20-tetraphenylporphyrinato)copper(II) (3cb) (30 mg, yield-ca 10%). 3cc can befurther purified by preparative TLC.

14172-91-9 5,10,15,20-Tetraphenyl-21H,23H-porphine copper(II) 3722750, acopper-catalyst compound, is more and more widely used in various fields.

Reference£º
Article; Mikus, Agnieszka; Rosa, Mariusz; Ostrowski, Stanis?aw; Molecules; vol. 24; 5; (2019);,
Copper catalysis in organic synthesis – NCBI
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”