1423875-77-7

Basic information

• Product Name: [(2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl)Ir(OAc)H]
• Synonyms: [(2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl)Ir(OAc)H]
• CAS NO: 1423875-77-7
• Molecular Weight: 551.665
• Mol File: 1423875-77-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: [(2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl)Ir(OAc)H](CAS DataBase Reference)
• NIST Chemistry Reference: [(2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl)Ir(OAc)H](1423875-77-7)
• EPA Substance Registry System: [(2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl)Ir(OAc)H](1423875-77-7)

Safety Data

• Hazardous Substances Data: 1423875-77-7(Hazardous Substances Data)

Upstream product

• 1579297-38-3 (2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl)Ir(acetate)(OOH) 
• 1380300-20-8 (2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl)Ir(OAc)(CH₂(CH₂)₆CH₃) 
• 111-65-9 octane 
• 929896-31-1 (Phebox)Ir(OAc)₂(OH₂) 

Downstream Products

• 1579297-41-8 (2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl)Ir(benzoate)H 

Relevant articles and documents

β-Hydride Elimination and C-H Activation by an Iridium Acetate Complex, Catalyzed by Lewis Acids. Alkane Dehydrogenation Cocatalyzed by Lewis Acids and [2,6-Bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl]iridium

NaBArF4 (sodium tetrakis[(3,5-trifluoromethyl)phenyl]borate) was found to catalyze reactions of (Phebox)IrIII(acetate) (Phebox = 2,6-bis(4,4-dimethyloxazolinyl)-3,5-dimethylphenyl) complexes, including (i) β-H elimination of (Phebox)Ir(OAc)(n-alkyl) to give (Phebox)Ir(OAc)(H) and the microscopic reverse, alkene insertion into the Ir-H bond of (Phebox)Ir(OAc)(H), and (ii) hydrogenolysis of the Ir-alkyl bond of (Phebox)Ir(OAc)(n-alkyl) and the microscopic reverse, C-H activation by (Phebox)Ir(OAc)(H), as indicated by H/D exchange experiments. For example, β-H elimination of (Phebox)Ir(OAc)(n-octyl) (2-Oc) proceeded on a time scale of minutes at -15 °C in the presence of (0.4 mM) NaBArF4 as compared with a very slow reaction at 125 °C in the absence of NaBArF4. In addition to NaBArF4, other Lewis acids are also effective. Density functional theory calculations capture the effect of the Na+ cation and indicate that it operates primarily by promoting κ2-κ1 dechelation of the acetate anion, which opens the coordination site needed to allow the observed reaction to proceed. In accord with the effect on these individual stoichiometric reactions, NaBArF4 was also found to cocatalyze, with (Phebox)Ir(OAc)(H), the acceptorless dehydrogenation of n-dodecane.

Alkane dehydrogenation by C-H activation at iridium(III)

Stoichiometric alkane dehydrogenation utilizing an IrIII pincer complex, (dmPhebox)Ir(OAc)2(OH2) (1a), has been described. The reaction between 1a and octane resulted in quantitative formation of (dmPhebox)Ir(OAc)(H) (3a) and octene. At early reaction times 1-octene is the major product, indicative of terminal C-H activation by 1a. In contrast to prior reports of alkane dehydrogenation with Ir, C-H bond activation occurs at IrIII and the dehydrogenation is not inhibited by nitrogen, olefin, or water.