386707-40-0

Basic information

• Product Name: (5,10,15,20-tetrakis(p-tolyl)porphyrinato)(methyl)iridium(III)
• Synonyms: (5,10,15,20-tetrakis(p-tolyl)porphyrinato)(methyl)iridium(III)
• CAS NO: 386707-40-0
• Molecular Weight: 876.095
• Mol File: 386707-40-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (5,10,15,20-tetrakis(p-tolyl)porphyrinato)(methyl)iridium(III)(CAS DataBase Reference)
• NIST Chemistry Reference: (5,10,15,20-tetrakis(p-tolyl)porphyrinato)(methyl)iridium(III)(386707-40-0)
• EPA Substance Registry System: (5,10,15,20-tetrakis(p-tolyl)porphyrinato)(methyl)iridium(III)(386707-40-0)

Safety Data

• Hazardous Substances Data: 386707-40-0(Hazardous Substances Data)

Upstream product

• 105139-33-1 (hydrido)(5,10,15,20-tetrakis(p-tolyl)porphyrinato)iridium(III) 
• 872415-81-1 (5,10,15,20-tetrakis(p-tolyl)porphyrinato)carbonyliridium(III) chloride 
• 6933-23-9 [α-¹³C]toluene 
• 108-88-3 toluene 
• 2037-26-5 ⁽²⁾H₈-toluene 
• 7789-20-0 water-d2 
• 106-42-3 para-xylene 
• 67-56-1 methanol 
• 17455-13-9 18-crown-6 ether 
• 106-46-7 para-dichlorobenzene 
• 108-90-7 chlorobenzene 
• 100-66-3 methoxybenzene 
• 872415-81-1 chloro(5,10,15,20-tetratolylporphyrinato)carbonyliridium(III) 
• 103-73-1 Phenetole 

Downstream Products

• 386707-30-8 CH₃Ir(C₂₀H₈N₄(C₆H₄CH₃)4)C₅H₅N 
• 386707-32-0 CH₃Ir(C₂₀H₈N₄(C₆H₄CH₃)4)(CH₃)2NC₅H₄N 
• 386707-33-1 CH₃Ir(C₂₀H₈N₄(C₆H₄CH₃)4)NCC₅H₄N 
• 386707-31-9 CH₃Ir(C₂₀H₈N₄(C₆H₄CH₃)4)(CH₃)3CC₅H₄N 
• 928267-36-1 (5,10,15,20-tetratolylporphyrinato)(ethylformyl)iridium(III) 
• 928267-45-2 (5,10,15,20-tetratolylporphyrinato)(benzoyl)iridium(III) toluene 
• 928267-48-5 (5,10,15,20-tetratolylporphyrinato)(4-fluorobenzoyl)iridium(III) toluene 
• 928267-43-0 (5,10,15,20-tetratolylporphyrinato)(4-chlorobenzoyl)iridium(III) 
• 928267-40-7 (5,10,15,20-tetratolylporphyrinato)(4-methylbenzoyl)iridium(III) 
• 928267-41-8 (5,10,15,20-tetratolylporphyrinato)(4-tert-butylbenzoyl)iridium(III) 
• 928267-44-1 (5,10,15,20-tetratolylporphyrinato)(4-(α,α,α-trifluoromethyl)benzoyl)iridium(III) 
• 872415-82-2 Ir(ttp)CH₂COPh 
• 928267-35-0 Ir(ttp)COPh 
• 928267-42-9 Ir(ttp)CO(4-F-Ph) 

Relevant articles and documents

User-friendly aerobic reductive alkylation of iridium(III) porphyrin chloride with potassium hydroxide: Scope and mechanism

Alkylation of iridium 5,10,15,20-tetrakistolylporphyrinato carbonyl chloride, Ir(ttp)Cl(CO) (1), with 1°, 2° alkyl halides was achieved to give (ttp)Ir-alkyls in good yields under air and water compatible conditions by utilizing KOH as the cheap reducing agent. The reaction rate followed the order: RCl N2 pathway by [IrI(ttp)]-. Ir(ttp)-adamantyl was obtained under N2 when 1-bromoadamantane was utilized, which could only undergo bromine atom transfer pathway. Mechanistic investigations reveal a substrate dependent pathway of SN2 or halogen atom transfer.

Alkyl Carbon-Oxygen Bond Cleavage of Aryl Alkyl Ethers by Iridium-Porphyrin and Rhodium-Porphyrin Complexes in Alkaline Media

Alkyl C-O bond cleavage in aryl alkyl ethers was achieved with Rh(ttp)Cl (1a; ttp = 5,10,15,20-tetrakis(p-tolyl)porphyrinato dianion) together with competitive alkyl C-H bond activation in alkaline media. In contrast, selective alkyl C-O bond cleavage occurred with the iridium-porphyrin Ir(ttp)(CO)Cl (1b)/KOH. Mechanistic investigations indicate the coexistence of MI(ttp)- and M2II(ttp)2 (M = Rh, Ir) under basic conditions. With a weaker Rh(ttp)-Rh(ttp) bond, RhII(ttp)· metalloradical exists in an appreciable amount to cleave the alkyl C-H bond, competing with the alkyl C-O bond cleavage via RhI(ttp)-. In contrast, the more nucleophilic IrI(ttp)- cleaves the alkyl C-O bond exclusively.

Base-promoted selective aryl C-Cl cleavage by iridium(III) porphyrins via a metalloradical ipso addition-elimination mechanism

Base-promoted aryl carbon-chlorine bond (Ar-Cl) cleavage by iridium(III) porphyrin carbonyl chloride (IrIII(ttp)(CO)Cl; ttp = 5,10,15,20-tetrakis(p-tolyl)porphyrinato dianion) was achieved in the presence of K2CO3 to give iridium(III) porphyrin aryls (Ir III(ttp)Ar). Mechanistic studies revealed that K2CO 3 promotes the reduction of Ir(ttp)(CO)Cl to give the iridium(II) porphyrin dimer intermediate [IrII(ttp)2. [Ir(ttp) 2 is the source of IrII(ttp) metalloradical, which cleaves Ar-Cl to give Ir(ttp)Ar and a chlorine radical (Cl?) via radical ipso substitution in an addition-elimination pathway. Cl ? reacts with [Ir(ttp)2 to yield Ir(ttp)Cl for subsequent base-promoted reduction and Ir(ttp) for radical chain propagation. Additionally, the base-promoted Ar-Cl cleavage of chlorobenzene (PhCl) by Ir(ttp)(CO)Cl gives both Ir(ttp)Ph and 1,4-bis-iridium(III)-porphyrin benzene, IrIII(ttp)(p-C6H4)IrIII(ttp). The reactive Cl? can simultaneously react with PhCl via homolytic aromatic substitution to give 1,4-dichlorobenzene, which further undergoes double Ar-Cl cleavage to form Ir(ttp)(p-C6H4)Ir(ttp).