905917

Sigma-Aldrich

(Ir[Me(Me)ppy]2(dtbpy))PF6

Empirical Formula (Hill Notation):
C44H48F6IrN4P
CAS Number:
Molecular Weight:
970.06

form

powder

reaction suitability

core: iridium
reagent type: catalyst
reaction type: Photocatalysis

photocatalyst activation

465 nm

SMILES string

F[P-](F)(F)(F)(F)F.CC1=CC([Ir+]([N]2=C3C=C(C)C=C2)(C4=C5C=CC(C)=C4)([N]6=C7C=C(C(C)(C)C)C=C6)([N]8=C7C=C(C(C)(C)C)C=C8)[N]9=C5C=C(C)C=C9)=C3C=C1

Application

(Ir[Me(Me)ppy]2(dtbpy))PF6 or Ir(dmppy)2(dtbbpy)PF6 is an iridium photoredox catalyst that facilitates a variety of transformations using visible light, including the α- and β-alkylation of aldehydes.

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Direct, enantioselective α-alkylation of aldehydes using simple olefins.
Capacci AG, et al.
Nature Chemistry, 9(11), 1073-1073 (2017)
Direct β -alkylation of aldehydes via photoredox organocatalysis.
Terrett JA, et al.
Journal of the American Chemical Society, 136(19), 6858-6861 (2014)
Jack A Terrett et al.
Journal of the American Chemical Society, 136(19), 6858-6861 (2014-04-24)
Direct β-alkylation of saturated aldehydes has been accomplished by synergistically combining photoredox catalysis and organocatalysis. Photon-induced enamine oxidation provides an activated β-enaminyl radical intermediate, which readily combines with a wide range of Michael acceptors to produce β-alkyl aldehydes in a...
Zachary C Litman et al.
Nature, 560(7718), 355-359 (2018-08-17)
Living organisms rely on simultaneous reactions catalysed by mutually compatible and selective enzymes to synthesize complex natural products and other metabolites. To combine the advantages of these biological systems with the reactivity of artificial chemical catalysts, chemists have devised sequential...
Andrew G Capacci et al.
Nature chemistry, 9(11), 1073-1077 (2017-10-25)
Although the α-alkylation of ketones has already been established, the analogous reaction using aldehyde substrates has proven surprisingly elusive. Despite the structural similarities between the two classes of compounds, the sensitivity and unique reactivity of the aldehyde functionality has typically...

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