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Heterolytic Oxidative Addition of sp2and sp3C-H Bonds by Metal-Ligand Cooperation with an Electron-Deficient Cyclopentadienone Iridium Complex
Oxidative addition reactions of C-H bonds that generate metal-carbon-bond-containing reactive intermediates have played essential roles in the field of organometallic chemistry. Herein, we prepared a cyclopentadienone iridium(I) complex 1 designed for oxidative C-H bond additions. The complex cleaves the various sp2 and sp3 C-H bonds including those in hexane and methane as inferred from their H/D exchange reactions. The hydroxycyclopentadienyl(nitromethyl)iridium(III) complex 2 was formed when the complex was treated with nitromethane, which highlights this elementary metal-ligand cooperative C-H bond oxidative addition reaction. Mechanistic investigations suggested the C-H bond cleavage is mediated by polar functional groups in substrates or another iridium complex. We found that ligands that are more electron-deficient lead to more favorable reactions, in sharp contrast to classical metal-centered oxidative additions. This trend is in good agreement with the proposed mechanism, in which C-H bond cleavage is accompanied by two-electron transfer from the metal center to the cyclopentadienone ligand. The complex was further applied to catalytic transfer-dehydrogenation of tetrahydrofuran (THF).
Higashi, Takuya,Kusumoto, Shuhei,Nozaki, Kyoko
supporting information
p. 12999 - 13004
(2021/08/16)

H/D exchange processes catalyzed by an iridium-pincer complex
A PNP-pincer iridium dihydride performs the H/D exchange between aromatic substrates and tertiary hydrosilanes and D2O or C6D 6. Complete incorporation of deuterium into sterically accessible Car-H and Si-H bonds was observed at a moderate temperature of 80 °C.
Iluc, Vlad M.,Fedorov, Alexey,Grubbs, Robert H.
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p. 39 - 41
(2012/04/10)

Chemical Properties

Appearance/Colour :colorless to light yellow liqui
Boiling Point: 31.4 °C at 760 mmHg
Flash Point:−32 °F
Density: 0.998 g/cm³
Solubility:Chloroform (Sparingly), DMSO (Slightly), Methanol (Sparingly)
Storage Temp.:0-6°C
Vapor Pressure: 9.63 psi ( 20 °C)
Refractive Index: n20/D 1.4202(lit.)
PSA: 13.14000
LogP: 1.27960

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Chemical Properties

Appearance/Colour :colorless to light yellow liqui

Boiling Point: 31.4 °C at 760 mmHg

Flash Point:−32 °F

Density: 0.998 g/cm³

Solubility:Chloroform (Sparingly), DMSO (Slightly), Methanol (Sparingly)

Storage Temp.:0-6°C

Vapor Pressure: 9.63 psi ( 20 °C)

Refractive Index: n20/D 1.4202(lit.)

PSA: 13.14000

LogP: 1.27960

Global suppliers and manufacturers of 6142-90-1total 7 suppliers on LookChem

Article Database

6142-90-1

Articles about 6142-90-1Total 2 be found

More Articles about upstream products of 6142-90-1

Chemical Properties

Appearance/Colour :colorless to light yellow liqui

Boiling Point: 31.4 °C at 760 mmHg

Flash Point:−32 °F

Density: 0.998 g/cm3

Solubility:Chloroform (Sparingly), DMSO (Slightly), Methanol (Sparingly)

Storage Temp.:0-6°C

Vapor Pressure: 9.63 psi ( 20 °C)

Refractive Index: n20/D 1.4202(lit.)

PSA: 13.14000

LogP: 1.27960

Global suppliers and manufacturers of 6142-90-1total 7 suppliers on LookChem

Density: 0.998 g/cm³