872415-72-0

Basic information

• Product Name: (5,10,15,20-tetra-p-tolylporphyrinato)ethyliridium(III)
• Synonyms: (5,10,15,20-tetra-p-tolylporphyrinato)ethyliridium(III)
• CAS NO: 872415-72-0
• Molecular Weight: 890.122
• Mol File: 872415-72-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (5,10,15,20-tetra-p-tolylporphyrinato)ethyliridium(III)(CAS DataBase Reference)
• NIST Chemistry Reference: (5,10,15,20-tetra-p-tolylporphyrinato)ethyliridium(III)(872415-72-0)
• EPA Substance Registry System: (5,10,15,20-tetra-p-tolylporphyrinato)ethyliridium(III)(872415-72-0)

Safety Data

• Hazardous Substances Data: 872415-72-0(Hazardous Substances Data)

Upstream product

• 78-93-3 butanone 
• 96-22-0 pentan-3-one 
• 872415-81-1 chloro(5,10,15,20-tetratolylporphyrinato)carbonyliridium(III) 
• 100-66-3 methoxybenzene 
• 103-73-1 Phenetole 
• 622-85-5 propoxybenzene 
• 64-17-5 ethanol 

Downstream Products

• 386707-40-0 (5,10,15,20-tetrakis(p-tolyl)porphyrinato)(methyl)iridium(III) 

Relevant articles and documents

Base-Promoted C-O Bond Cleavage of Primary Alcohols by Iridium(III) Porphyrin Chloride

Various Ir(por)-benzyls and Ir(por)-alkyls (por = porphyrinato dianion ligand) were successfully synthesized with benzyl and 1° alkyl alcohols by C-O bond cleavage with Ir(ttp)(CO)Cl (ttp = 5,10,15,20-tetraphenylporphyrinato dianion) in alkaline media. The alkylation products were afforded in up to 92% yields. Mechanistic investigations suggest that both the Ir(ttp)- anion and Ir(ttp)H are key intermediates via a hydrogen-borrowing pathway.

Scope and mechanism of carbonyl carbon and α-carbon bond cleavage of ketones by Iridium(III) porphyrin complexes

Chemoselective carbonyl carbon and α-carbon bond activation (CCA) of ketones (RCOR) was successfully achieved with various iridium(III) tetrakis-4-tolylporphyrinato complexes Ir(ttp)X (X = (BF4)(CO), Cl(CO), and Me) to give the corresponding Ir(ttp)COR (R = Ar, Me, or Et) and Ir(ttp)R (R = Me or Et) complexes. Ir(ttp)(BF4)(CO) exhibited the highest reactivity toward CCA, as it possesses a higher Lewis acidity in catalyzing the aldol condensation of ketones to give water, which hydrolyzes the kinetic products, C-H bond activation (CHA) complexes, into the proposed Ir(ttp)OH for a subsequent CCA process. The CCA step is nonregioselective in giving both Ir(ttp)R and Ir(ttp)COR. However, Ir(ttp)R was kinetically less stable toward hydrolysis to give Ir(ttp)OH. Thus, only Ir(ttp)COR was observed as the sole CCA product.