1610606-40-0

Basic information

• Product Name: (Ph₃P)Au(4-Me-C₆H₄)(CF₃)(I)
• Synonyms: (Ph₃P)Au(4-Me-C₆H₄)(CF₃)(I)
• CAS NO: 1610606-40-0
• Molecular Weight: 746.301
• Mol File: 1610606-40-0.mol

Chemical Properties

• CAS DataBase Reference: (Ph₃P)Au(4-Me-C₆H₄)(CF₃)(I)(CAS DataBase Reference)
• NIST Chemistry Reference: (Ph₃P)Au(4-Me-C₆H₄)(CF₃)(I)(1610606-40-0)
• EPA Substance Registry System: (Ph₃P)Au(4-Me-C₆H₄)(CF₃)(I)(1610606-40-0)

Safety Data

• Hazardous Substances Data: 1610606-40-0(Hazardous Substances Data)

Upstream product

• 2314-97-8 iodotrifluoromethane 
• 40667-81-0 (4-methylphenyl)gold(triphenylphosphine) 

Downstream Products

• 60898-04-6 triluoromethyl(triphenylphosphine)gold(I) 
• 624-31-7 4-tolyl iodide 
• 1610606-42-2 C₂₆H₇⁽²⁾H₁₅AuF₃IP 
• 6140-17-6 4-methylbenzotrifluoride 

Relevant articles and documents

Halide-Dependent Mechanisms of Reductive Elimination from Gold(III)

Two unique organometallic halide series (Ph3P)Au(4-Me-C6H4)(CF3)(X) and (Cy3P)Au(4-F-C6H4)(CF3)(X) (X = I, Br, Cl, F) have been synthesized. The PPh3-supported complexes can undergo both Caryl-X and Caryl-CF3 reductive elimination. Mechanistic studies of thermolysis at 122 °C reveal a dramatic reactivity and kinetic selectivity dependence on halide ligand. For X = I or F, zero-order kinetic behavior is observed, while for X = Cl or Br, kinetic studies implicate product catalysis. The selectivity for Caryl-CF3 bond formation increases in the order X = I aryl-I bond formation when X = I, and exclusively Caryl-CF3 bond formation when X = F. Thermodynamic measurements show that Au(III)-X bond dissociation energies increase in the order X = I aryl-X and Caryl-CF3 reductive elimination. (Graph Presented).

Photoinitiated oxidative addition of CF3I to gold(I) and facile aryl-CF3 reductive elimination

Herein we report the mechanism of oxidative addition of CF3I to Au(I), and remarkably fast Caryl-CF3 bond reductive elimination from Au(III) cations. CF3I undergoes a fast, formal oxidative addition to R3PAuR' (R = Cy, R' = 3,5-F2-C 6H4, 4-F-C6H4, C6H 5, 4-Me-C6H4, 4-MeO-C6H4, Me; R = Ph, R' = 4-F-C6H4, 4-Me-C6H 4). When R' = aryl, complexes of the type R3PAu(aryl) (CF3)I can be isolated and characterized. Mechanistic studies suggest that near-ultraviolet light (λmax = 313 nm) photoinitiates a radical chain reaction by exciting CF3I. Complexes supported by PPh3 undergo reversible phosphine dissociation at 110 °C to generate a three-coordinate intermediate that undergoes slow reductive elimination. These processes are quantitative and heavily favor C aryl-I reductive elimination over Caryl-CF3 reductive elimination. Silver-mediated halide abstraction from all complexes of the type R3PAu(aryl)(CF3)I results in quantitative formation of Ar-CF3 in less than 1 min at temperatures as low as -10 °C.