[Ir(dtbbpy)(ppy)2][PF6]

Reaction

1. This Iridium catalyst is used in the synthesis of β-amidovinyl sulfones via visible-light photoredox catalysis.
2. Numerous uses of this photoredox catalyst are reported

Uses

[Ir(dtbbpy)(ppy)₂]PF₆ is an iridium-based photocatalyst which is used to drive various photochemical reactions such as:

• Coupling of N-arylamines and nitroalkanes via an oxidative aza-Henry reaction.
• Atom transfer radical addition (ATRA) of haloalkanes to alkenes and alkynes.
• Conversion of 2-bromoanilides to the corresponding 3,3-disubstituted oxindoles.
• Aryl-alkyl CC reductive cross-coupling reactions.

reaction suitability

core: iridium
reaction type: Photocatalysis
reagent type: catalyst

Synthesis

Dichlorobridged dimer (0.1 mmol) was reacted with the appropriate neutral ligand (0.22 mmol) in ethylene glycol (5.0 mL) at reflux (150C) for 15 h with continuous stirring. After cooling to room temperature, the mixture was transferred to a dispensing funnel with water (3 x 30 mL) and washed (except in the case of C^N) dtbppy with ether (3 x 50 mL). The aqueous layer was heated to 70C for 5 min using a heat gun to remove residual organic solvent. The vessel was then placed on ice and 10 mL of aqueous ammonium hexafluorophosphate (1.0 g in 10 mL of deionized water) was slowly added to the reaction mixture to obtain a colored suspension. The precipitate was collected by suction filtration and allowed to air dry overnight. The product was recrystallized by acetonitrile:ether vapor diffusion (except for C^N) dtbppy, where hexane:acetone vapor diffusion was used) and dried under vacuum (100C) for 24 hr to give the pure product (4,4'-di-tert-butyl-2,2'-bipyridine)bis[(2-pyridyl)phenyl]iridium(III) hexafluorophosphate (yield: 68- 80%).