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CAS 1973375-72-2

[5,5'-Bis(trifluoromethyl)-2,2'-bipyridine-kappa~2~N~1~,N~1'~][bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-kappaN]phenyl-kappaC~1~]]iridium Hexafluorophosphate TCI B6451

[5,5'-Bis(trifluoromethyl)-2,2'-bipyridine-kappa~2~N~1~,N~1'~][bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-kappaN]phenyl-kappaC~1~]]iridium Hexafluorophosphate TCI B6451

Chemical Identity

Other names
[5,5'-Bis(trifluoromethyl)-2,2'-bipyridine-kappaN,kappaN]bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-kappaN]phenyl] Iridium Hexafluorophosphate · [Ir(dFCF3ppy)2-(5,5′-dCF3bpy)]PF6
CAS No.
1973375-72-2
Formula
C36H16F22IrN4P
Molecular weight
1,145.71 g/mol
Purity
>95.0%(HPLC)(qNMR)
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TCI B6451 (CAS 1973375-72-2) is a cationic cyclometalated iridium complex supplied as its hexafluorophosphate salt for use as a visible-light photocatalyst. The fluorinated and trifluoromethylated ligands tune the excited-state redox properties, supporting demanding single-electron transfer and energy transfer processes. It is widely applied in photoredox and metallaphotoredox methodologies, including nickel-catalyzed cross-coupling under mild conditions. Store the catalyst tightly closed in a cool, dry place protected from light, and weigh it in a fume hood using standard personal protective equipment.

Advantages (TCI brochure)

  • Highly oxidizing excited state compared to conventional iridium catalysts

From the TCI brochure

  • Catalytic carbocation generation via mesolytic cleavage of alkoxyamine radical cations (ref 1)
  • Alkene aminoarylation with arylsulfonylacetamide bifunctional reagents (ref 2)
  • Light-driven out-of-equilibrium isomerization and catalytic C-C bond cleavage (ref 3)
  • Synthesis of alpha-aminosilanes by visible-light multicomponent radical cross-coupling (ref 4)
  • Single and multiple deuteration of unactivated C(sp3)-H bonds (ref 5)

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Data from the TCI brochure

PC*/PC-+1.68 V (vs. SCE)
PC+/PC*-0.43 V (vs. SCE)
PC+/PC+1.94 V (vs. SCE)
PC/PC--0.69 V (vs. SCE)

Source: TCI brochure RR187 (2023-07-21)

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  • Heuer et al. (1990). Preparation of bis[2,4-bis(trifluoromethyl)phenyl]fluorophosphine and 2,4-bis[trifluoromethyl) phenyl-[2,6-bis(trifluoromethyl)phenyl]-fluorophosphine - two distillable monofluorophosphines. Structure of cis-dichloro-bis[2,4-bis(trifluoromethyl)phenyl)fluorophosphino]platinum(II). Journal of Fluorine Chemistry doi:10.1016/s0022-1139(00)80993-8
  • HEUER et al. (1990). ChemInform Abstract: Preparation of Bis(2,4‐bis(trifluoromethyl)phenyl)fluorophosphine (III) and 2,4‐Bis(trifluoromethyl)phenyl(2,6‐bis(trifluoromethyl)phenyl)fluorophosphine (IV) ‐ Two Distillable Monofluorophosphines. Structure of cis‐Dichlorobis(bis(2,4‐bis‐(trifluoromethyl)phenyl)fluorophosphino)platinum(II) (VI).. ChemInform doi:10.1002/chin.199027261
  • Han et al. (2018). Efficient electroluminescence of bluish green iridium complexes with 2-(3,5-bis(trifluoromethyl)phenyl)pyrimidine and 2-(3,5-bis(trifluoromethyl)phenyl)-5-fluoropyrimidine as the main ligands. Inorganic Chemistry Frontiers doi:10.1039/c8qi00294k

References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.

References cited in the TCI brochure

  1. Qilei Zhu. Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations Angewandte Chemie International Edition, 2016. doi:10.1002/anie.201604619
  2. Timothy M. Monos. Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation Science, 2018. doi:10.1126/science.aat2117
  3. Eisuke Ota. A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C–C Bond Cleavage Reactions Journal of the American Chemical Society, 2019. doi:10.1021/jacs.8b12552
  4. Xiaoye Yu. Direct Access to α‐Aminosilanes Enabled by Visible‐Light‐Mediated Multicomponent Radical Cross‐Coupling Angewandte Chemie International Edition, 2021. doi:10.1002/anie.202109252
  5. Nian Li. Highly selective single and multiple deuteration of unactivated C(sp3)-H bonds Nature Communications, 2022. doi:10.1038/s41467-022-31956-3