Synthesis and Reactivity of Methylpalladium Complexes Bearing a Partially Saturated IzQO Ligand

Shumpei Akita; Ryo Nakano; Shingo Ito; Kyoko Nozaki

doi:10.1021/acs.organomet.8b00263

Synthesis and Reactivity of Methylpalladium Complexes Bearing a Partially Saturated IzQO Ligand

Shumpei Akita, Ryo Nakano, Shingo Ito, Kyoko Nozaki^*

^*Corresponding author for this work

The University of Tokyo

Research output: Contribution to journal › Article › peer-review

24 Citations (Scopus)

Abstract

A saturated N-heterocyclic carbene-phenolate bidentate ligand, 3,3a,4,5-tetrahydroimidazo[1,5-a]quinolin-9-olate-1-ylidene (SIzQO), was synthesized and characterized. The SIzQO ligand was then treated with PdClMe(pyridine)₂ and [Pd(μ-Cl)Me(2,6-lutidine)]₂, which afforded C,C-cis-(SIzQO)PdMe(pyridine) and the thermodynamically unstable trans isomer C,C-trans-(SIzQO)PdMe(2,6-lutidine), respectively. The latter isomerizes at 40 °C into the corresponding cis isomer via a dissociative mechanism. These palladium/SIzQO complexes catalyze the polymerization of ethylene at 100-120 °C, although the catalytic activity is lower than that of a previously reported palladium/imidazo[1,5-a]quinolin-9-olate-1-ylidene (IzQO) system.

Original language	English
Pages (from-to)	2286-2296
Number of pages	11
Journal	Organometallics
Volume	37
Issue number	14
DOIs	https://doi.org/10.1021/acs.organomet.8b00263
Publication status	Published - Jul 23 2018
Externally published	Yes

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Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus Subject Areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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title = "Synthesis and Reactivity of Methylpalladium Complexes Bearing a Partially Saturated IzQO Ligand",

abstract = "A saturated N-heterocyclic carbene-phenolate bidentate ligand, 3,3a,4,5-tetrahydroimidazo[1,5-a]quinolin-9-olate-1-ylidene (SIzQO), was synthesized and characterized. The SIzQO ligand was then treated with PdClMe(pyridine)2 and [Pd(μ-Cl)Me(2,6-lutidine)]2, which afforded C,C-cis-(SIzQO)PdMe(pyridine) and the thermodynamically unstable trans isomer C,C-trans-(SIzQO)PdMe(2,6-lutidine), respectively. The latter isomerizes at 40 °C into the corresponding cis isomer via a dissociative mechanism. These palladium/SIzQO complexes catalyze the polymerization of ethylene at 100-120 °C, although the catalytic activity is lower than that of a previously reported palladium/imidazo[1,5-a]quinolin-9-olate-1-ylidene (IzQO) system.",

author = "Shumpei Akita and Ryo Nakano and Shingo Ito and Kyoko Nozaki",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.organomet.8b00263",

language = "English",

volume = "37",

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T1 - Synthesis and Reactivity of Methylpalladium Complexes Bearing a Partially Saturated IzQO Ligand

AU - Akita, Shumpei

AU - Nakano, Ryo

AU - Ito, Shingo

AU - Nozaki, Kyoko

PY - 2018/7/23

Y1 - 2018/7/23

N2 - A saturated N-heterocyclic carbene-phenolate bidentate ligand, 3,3a,4,5-tetrahydroimidazo[1,5-a]quinolin-9-olate-1-ylidene (SIzQO), was synthesized and characterized. The SIzQO ligand was then treated with PdClMe(pyridine)2 and [Pd(μ-Cl)Me(2,6-lutidine)]2, which afforded C,C-cis-(SIzQO)PdMe(pyridine) and the thermodynamically unstable trans isomer C,C-trans-(SIzQO)PdMe(2,6-lutidine), respectively. The latter isomerizes at 40 °C into the corresponding cis isomer via a dissociative mechanism. These palladium/SIzQO complexes catalyze the polymerization of ethylene at 100-120 °C, although the catalytic activity is lower than that of a previously reported palladium/imidazo[1,5-a]quinolin-9-olate-1-ylidene (IzQO) system.

AB - A saturated N-heterocyclic carbene-phenolate bidentate ligand, 3,3a,4,5-tetrahydroimidazo[1,5-a]quinolin-9-olate-1-ylidene (SIzQO), was synthesized and characterized. The SIzQO ligand was then treated with PdClMe(pyridine)2 and [Pd(μ-Cl)Me(2,6-lutidine)]2, which afforded C,C-cis-(SIzQO)PdMe(pyridine) and the thermodynamically unstable trans isomer C,C-trans-(SIzQO)PdMe(2,6-lutidine), respectively. The latter isomerizes at 40 °C into the corresponding cis isomer via a dissociative mechanism. These palladium/SIzQO complexes catalyze the polymerization of ethylene at 100-120 °C, although the catalytic activity is lower than that of a previously reported palladium/imidazo[1,5-a]quinolin-9-olate-1-ylidene (IzQO) system.

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ER -

Synthesis and Reactivity of Methylpalladium Complexes Bearing a Partially Saturated IzQO Ligand

Abstract

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