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747769

Sigma-Aldrich

[Ir(dtbbpy)(ppy)2]PF6

Synonym(s):

[Ir(dtbbpy)(ppy)2][PF6], Ir Photocatalyst, [4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis[2-(2-pyridinyl-N)phenyl-C]iridium(III) hexafluorophosphate

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About This Item

Empirical Formula (Hill Notation):
C40H40F6IrN4P
CAS Number:
676525-77-2
Molecular Weight:
913.95
UNSPSC Code:
12352300

form

powder

Quality Level

100

reaction suitability

core: iridium
reaction type: Photocatalysis
reagent type: catalyst

photocatalyst activation

455 nm

storage temp.

2-8°C

SMILES string

CC(C1=CC=[N]([Ir]2([N]3=CC=C(C=C34)C(C)(C)C)([N]5=CC=CC=C5C6=CC=CC=C62)(C7=CC=CC=C78)[N]9=C8C=CC=C9)C4=C1)(C)C.FP(F)(F)(F)(F)F

InChI

1S/C18H24N2.2C11H8N.F6P.Ir/c1-17(2,3)13-7-9-19-15(11-13)16-12-14(8-10-20-16)18(4,5)6;2*1-2-6-10(7-3-1)11-8-4-5-9-12-11;1-7(2,3,4,5)6;/h7-12H,1-6H3;2*1-6,8-9H;;

InChI key

DZARMRZNOUWGQE-UHFFFAOYSA-N

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Application

[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 C−C reductive cross-coupling reactions.
Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Photoredox-Assisted Reductive Cross-Coupling: Mechanistic Insight into Catalytic Aryl-Alkyl Cross-Couplings.
Paul, Avishek et al.
The Journal of Organic Chemistry, 82(4), 1996-2003 (2017)
Synthesis of oxindoles via visible light photoredox catalysis.
Ju, Xuhui et al.
Organic & Biomolecular Chemistry, 10(3), 498-501 (2012)
Visible light-mediated atom transfer radical addition via oxidative and reductive quenching of photocatalysts.
Wallentin, Carl-Johan et al.
Journal of the American Chemical Society, 134(21), 8875-8884 (2012)
Visible-light photoredox catalysis: Aza-Henry reactions via C- H functionalization.
Condie, Allison G et al.
Journal of the American Chemical Society, 132(5), 1464-1465 (2010)

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