Preparation and activity of recyclable polymer-supported ruthenium olefin metathesis catalysts

L  Jafarpour; M P  Heck; C  Baylon; H M  Lee; C  Mioskowski; Steven Patrick Nolan

doi:10.1021/om0109206

Preparation and activity of recyclable polymer-supported ruthenium olefin metathesis catalysts

L Jafarpour, M P Heck, C Baylon, H M Lee, C Mioskowski, Steven Patrick Nolan

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

Abstract

The ruthenium catalysts (PCy3)(2)Ru(=C(H)Ph)Cl-2 (1), (PCy3)Ru(IMes)(=C(H)Ph)Cl-2 (2), (PCy3)Ru(SIMes)(=C(H)Ph)Cl-2 (3), (PCyp(3))Ru(IMes)(=CHCH=C(CH3)(2))Cl-2 (4), and (PCy3)Ru(IPr)(3-phenylindenylid-1-ene)Cl-2 (5), where IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, Cy = cyclohexyl, and Cpy = cyclopentyl, have been grafted to polymer supports and found to be effective heterogeneous catalysts for ring-closing metathesis. In some cases, they are recyclable, show comparable reactivity to their homogeneous counterparts, tolerate functional groups, and perform very well with unsubstituted dienes.

Original language	English
Pages (from-to)	671-679
Number of pages	9
Journal	Organometallics
Volume	21
Issue number	4
DOIs	https://doi.org/10.1021/om0109206
Publication status	Published - 18 Feb 2002

Keywords

RING-CLOSING METATHESIS
CYCLIC ENOL ETHERS
ORGANIC-SYNTHESIS
ASYMMETRIC HYDROFORMYLATION
FUNCTIONALIZED OLEFINS
NITROGEN-HETEROCYCLES
ALKYLIDENE COMPLEXES
CARBENE COMPLEXES
ACYCLIC OLEFINS
NEW-GENERATION

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@article{f01a2ce318164981b771a3b8d0aeb254,

title = "Preparation and activity of recyclable polymer-supported ruthenium olefin metathesis catalysts",

abstract = "The ruthenium catalysts (PCy3)(2)Ru(=C(H)Ph)Cl-2 (1), (PCy3)Ru(IMes)(=C(H)Ph)Cl-2 (2), (PCy3)Ru(SIMes)(=C(H)Ph)Cl-2 (3), (PCyp(3))Ru(IMes)(=CHCH=C(CH3)(2))Cl-2 (4), and (PCy3)Ru(IPr)(3-phenylindenylid-1-ene)Cl-2 (5), where IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, Cy = cyclohexyl, and Cpy = cyclopentyl, have been grafted to polymer supports and found to be effective heterogeneous catalysts for ring-closing metathesis. In some cases, they are recyclable, show comparable reactivity to their homogeneous counterparts, tolerate functional groups, and perform very well with unsubstituted dienes.",

keywords = "RING-CLOSING METATHESIS, CYCLIC ENOL ETHERS, ORGANIC-SYNTHESIS, ASYMMETRIC HYDROFORMYLATION, FUNCTIONALIZED OLEFINS, NITROGEN-HETEROCYCLES, ALKYLIDENE COMPLEXES, CARBENE COMPLEXES, ACYCLIC OLEFINS, NEW-GENERATION",

author = "L Jafarpour and Heck, {M P} and C Baylon and Lee, {H M} and C Mioskowski and Nolan, {Steven Patrick}",

year = "2002",

month = feb,

day = "18",

doi = "10.1021/om0109206",

language = "English",

volume = "21",

pages = "671--679",

journal = "Organometallics",

issn = "0276-7333",

publisher = "American Chemical Society (ACS)",

number = "4",

}

TY - JOUR

T1 - Preparation and activity of recyclable polymer-supported ruthenium olefin metathesis catalysts

AU - Jafarpour, L

AU - Heck, M P

AU - Baylon, C

AU - Lee, H M

AU - Mioskowski, C

AU - Nolan, Steven Patrick

PY - 2002/2/18

Y1 - 2002/2/18

N2 - The ruthenium catalysts (PCy3)(2)Ru(=C(H)Ph)Cl-2 (1), (PCy3)Ru(IMes)(=C(H)Ph)Cl-2 (2), (PCy3)Ru(SIMes)(=C(H)Ph)Cl-2 (3), (PCyp(3))Ru(IMes)(=CHCH=C(CH3)(2))Cl-2 (4), and (PCy3)Ru(IPr)(3-phenylindenylid-1-ene)Cl-2 (5), where IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, Cy = cyclohexyl, and Cpy = cyclopentyl, have been grafted to polymer supports and found to be effective heterogeneous catalysts for ring-closing metathesis. In some cases, they are recyclable, show comparable reactivity to their homogeneous counterparts, tolerate functional groups, and perform very well with unsubstituted dienes.

AB - The ruthenium catalysts (PCy3)(2)Ru(=C(H)Ph)Cl-2 (1), (PCy3)Ru(IMes)(=C(H)Ph)Cl-2 (2), (PCy3)Ru(SIMes)(=C(H)Ph)Cl-2 (3), (PCyp(3))Ru(IMes)(=CHCH=C(CH3)(2))Cl-2 (4), and (PCy3)Ru(IPr)(3-phenylindenylid-1-ene)Cl-2 (5), where IMes = 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene, SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, Cy = cyclohexyl, and Cpy = cyclopentyl, have been grafted to polymer supports and found to be effective heterogeneous catalysts for ring-closing metathesis. In some cases, they are recyclable, show comparable reactivity to their homogeneous counterparts, tolerate functional groups, and perform very well with unsubstituted dienes.

KW - RING-CLOSING METATHESIS

KW - CYCLIC ENOL ETHERS

KW - ORGANIC-SYNTHESIS

KW - ASYMMETRIC HYDROFORMYLATION

KW - FUNCTIONALIZED OLEFINS

KW - NITROGEN-HETEROCYCLES

KW - ALKYLIDENE COMPLEXES

KW - CARBENE COMPLEXES

KW - ACYCLIC OLEFINS

KW - NEW-GENERATION

U2 - 10.1021/om0109206

DO - 10.1021/om0109206

M3 - Article

SN - 0276-7333

VL - 21

SP - 671

EP - 679

JO - Organometallics

JF - Organometallics

IS - 4

ER -

Preparation and activity of recyclable polymer-supported ruthenium olefin metathesis catalysts

Abstract

Keywords

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