Isolation of trans-2,5-bis(methoxycarbonyl)ruthenacyclopentane by oxidative coupling of methyl acrylate on ruthenium(0) as an active intermediate for tail-to-tail selective catalytic dimerization

Masafumi Hirano; Yumiko Sakate; Nobuyuki Komine; Sanshiro Komiya; Martin A. Bennett

doi:10.1021/om9004065

Isolation of trans-2,5-bis(methoxycarbonyl)ruthenacyclopentane by oxidative coupling of methyl acrylate on ruthenium(0) as an active intermediate for tail-to-tail selective catalytic dimerization

Masafumi Hirano^*, Yumiko Sakate, Nobuyuki Komine, Sanshiro Komiya, Martin A. Bennett

^*Corresponding author for this work

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

38 Citations (Scopus)

Abstract

The trans-bis(methoxycarbonyl)ruthenacyclopentane complex [trans-Ru{C ²H{C(O¹)OMe}C³H₂C⁴H ₂C⁵H{C(O²)OMe}-K¹C ²,K¹O¹,K¹C⁵,μ-K ¹O²}(η⁴-1,5-COD)]₂ (2) and the acetonitrile adduct Ru[C²H(CO₂Me)CH₂CH ₂CH(CO₂Me)-K¹ C²,K¹ C⁵](η⁴-1,5-COD)(NCMe)₂ (3) have been obtained from the reaction of Ru(η⁶-naphthalene) (η⁴-1,5-COD) (1) with methyl acrylate and are active for the Ru(0)-catalyzed dimerization of methyl acrylate. Thus, complex 3 catalyzes the tail-totail dimerization of methyl acrylate in 52% yield at 140 °C in THF, suggesting that this dimerization proceeds by the oxidative coupling mechanism.

Original language	English
Pages (from-to)	4902-4905
Number of pages	4
Journal	Organometallics
Volume	28
Issue number	17
DOIs	https://doi.org/10.1021/om9004065
Publication status	Published - 14 Sept 2009

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@article{937e951da1f1441daff9cdbcb7aa7baf,

title = "Isolation of trans-2,5-bis(methoxycarbonyl)ruthenacyclopentane by oxidative coupling of methyl acrylate on ruthenium(0) as an active intermediate for tail-to-tail selective catalytic dimerization",

abstract = "The trans-bis(methoxycarbonyl)ruthenacyclopentane complex [trans-Ru{C 2H{C(O1)OMe}C3H2C4H 2C5H{C(O2)OMe}-K1C 2,K1O1,K1C5,μ-K 1O2}(η4-1,5-COD)]2 (2) and the acetonitrile adduct Ru[C2H(CO2Me)CH2CH 2CH(CO2Me)-K1 C2,K1 C5](η4-1,5-COD)(NCMe)2 (3) have been obtained from the reaction of Ru(η6-naphthalene) (η4-1,5-COD) (1) with methyl acrylate and are active for the Ru(0)-catalyzed dimerization of methyl acrylate. Thus, complex 3 catalyzes the tail-totail dimerization of methyl acrylate in 52% yield at 140 °C in THF, suggesting that this dimerization proceeds by the oxidative coupling mechanism.",

author = "Masafumi Hirano and Yumiko Sakate and Nobuyuki Komine and Sanshiro Komiya and Bennett, {Martin A.}",

year = "2009",

month = sep,

day = "14",

doi = "10.1021/om9004065",

language = "English",

volume = "28",

pages = "4902--4905",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society",

number = "17",

}

Isolation of trans-2,5-bis(methoxycarbonyl)ruthenacyclopentane by oxidative coupling of methyl acrylate on ruthenium(0) as an active intermediate for tail-to-tail selective catalytic dimerization. / Hirano, Masafumi; Sakate, Yumiko; Komine, Nobuyuki et al.
In: Organometallics, Vol. 28, No. 17, 14.09.2009, p. 4902-4905.

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

TY - JOUR

T1 - Isolation of trans-2,5-bis(methoxycarbonyl)ruthenacyclopentane by oxidative coupling of methyl acrylate on ruthenium(0) as an active intermediate for tail-to-tail selective catalytic dimerization

AU - Hirano, Masafumi

AU - Sakate, Yumiko

AU - Komine, Nobuyuki

AU - Komiya, Sanshiro

AU - Bennett, Martin A.

PY - 2009/9/14

Y1 - 2009/9/14

N2 - The trans-bis(methoxycarbonyl)ruthenacyclopentane complex [trans-Ru{C 2H{C(O1)OMe}C3H2C4H 2C5H{C(O2)OMe}-K1C 2,K1O1,K1C5,μ-K 1O2}(η4-1,5-COD)]2 (2) and the acetonitrile adduct Ru[C2H(CO2Me)CH2CH 2CH(CO2Me)-K1 C2,K1 C5](η4-1,5-COD)(NCMe)2 (3) have been obtained from the reaction of Ru(η6-naphthalene) (η4-1,5-COD) (1) with methyl acrylate and are active for the Ru(0)-catalyzed dimerization of methyl acrylate. Thus, complex 3 catalyzes the tail-totail dimerization of methyl acrylate in 52% yield at 140 °C in THF, suggesting that this dimerization proceeds by the oxidative coupling mechanism.

AB - The trans-bis(methoxycarbonyl)ruthenacyclopentane complex [trans-Ru{C 2H{C(O1)OMe}C3H2C4H 2C5H{C(O2)OMe}-K1C 2,K1O1,K1C5,μ-K 1O2}(η4-1,5-COD)]2 (2) and the acetonitrile adduct Ru[C2H(CO2Me)CH2CH 2CH(CO2Me)-K1 C2,K1 C5](η4-1,5-COD)(NCMe)2 (3) have been obtained from the reaction of Ru(η6-naphthalene) (η4-1,5-COD) (1) with methyl acrylate and are active for the Ru(0)-catalyzed dimerization of methyl acrylate. Thus, complex 3 catalyzes the tail-totail dimerization of methyl acrylate in 52% yield at 140 °C in THF, suggesting that this dimerization proceeds by the oxidative coupling mechanism.

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U2 - 10.1021/om9004065

DO - 10.1021/om9004065

M3 - Article

SN - 0276-7333

VL - 28

SP - 4902

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JO - Organometallics

JF - Organometallics

IS - 17

ER -

Isolation of trans-2,5-bis(methoxycarbonyl)ruthenacyclopentane by oxidative coupling of methyl acrylate on ruthenium(0) as an active intermediate for tail-to-tail selective catalytic dimerization

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