Synthesis and catalytic activity of supported acenaphthoimidazolylidene N-heterocyclic carbene ruthenium complex for ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP)

Antsar R. Hlil, Salvador Moncho Escriva, Robert Tuba, Khaled Elsaid, Györgyi Szarka, Edward Brothers, Robert H. Grubbs, Mohammed Al-Hashimi, Hassan S. Bazzi

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9 Citations (Scopus)

Abstract

Ruthenium catalyzed ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP) reactions using a supported bis(arylimino)acenaphthene N-heterocyclic carbene (BIAN-NHC) complex have been reported. The BIAN-NHC Ru-complex exhibits excellent catalytic activity and tolerates a wide range of substrates at low catalyst loadings. DFT calculations were also carried out on some selected key intermediates in the reaction mechanism to study the effect of having the conjugated aromatic moiety (BIAN-NHC) in the backbone of the complex. The newly synthesized BIAN-NHC Ru-complex shows comparable catalytic activities to the commercially available second generation Ru catalyst HG2. The recycled complex was reused for up to eight reaction cycles for the RCM of N,N-diallyl tosylamine affording a high average isolated yield, with lower levels of Ru contamination in the final product.[Figure Presented]

Original languageEnglish
Pages (from-to)100-107
Number of pages8
JournalJournal of Catalysis
Volume344
DOIs
Publication statusPublished - 1 Dec 2016

Fingerprint

Ruthenium
metathesis
Ring opening polymerization
carbenes
closing
ruthenium
catalytic activity
Catalyst activity
polymerization
Catalysts
rings
synthesis
Discrete Fourier transforms
Contamination
Substrates
catalysts
carbene
acenaphthene
contamination
cycles

Keywords

  • Acenaphthenequinone
  • Catalysis
  • Ring closing metathesis
  • Ring opening metathesis polymerization
  • Supported BIAN-NHC ruthenium complex

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry

Cite this

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title = "Synthesis and catalytic activity of supported acenaphthoimidazolylidene N-heterocyclic carbene ruthenium complex for ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP)",
abstract = "Ruthenium catalyzed ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP) reactions using a supported bis(arylimino)acenaphthene N-heterocyclic carbene (BIAN-NHC) complex have been reported. The BIAN-NHC Ru-complex exhibits excellent catalytic activity and tolerates a wide range of substrates at low catalyst loadings. DFT calculations were also carried out on some selected key intermediates in the reaction mechanism to study the effect of having the conjugated aromatic moiety (BIAN-NHC) in the backbone of the complex. The newly synthesized BIAN-NHC Ru-complex shows comparable catalytic activities to the commercially available second generation Ru catalyst HG2. The recycled complex was reused for up to eight reaction cycles for the RCM of N,N-diallyl tosylamine affording a high average isolated yield, with lower levels of Ru contamination in the final product.[Figure Presented]",
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author = "Hlil, {Antsar R.} and {Moncho Escriva}, Salvador and Robert Tuba and Khaled Elsaid and Gy{\"o}rgyi Szarka and Edward Brothers and Grubbs, {Robert H.} and Mohammed Al-Hashimi and Bazzi, {Hassan S.}",
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T1 - Synthesis and catalytic activity of supported acenaphthoimidazolylidene N-heterocyclic carbene ruthenium complex for ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP)

AU - Hlil, Antsar R.

AU - Moncho Escriva, Salvador

AU - Tuba, Robert

AU - Elsaid, Khaled

AU - Szarka, Györgyi

AU - Brothers, Edward

AU - Grubbs, Robert H.

AU - Al-Hashimi, Mohammed

AU - Bazzi, Hassan S.

PY - 2016/12/1

Y1 - 2016/12/1

N2 - Ruthenium catalyzed ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP) reactions using a supported bis(arylimino)acenaphthene N-heterocyclic carbene (BIAN-NHC) complex have been reported. The BIAN-NHC Ru-complex exhibits excellent catalytic activity and tolerates a wide range of substrates at low catalyst loadings. DFT calculations were also carried out on some selected key intermediates in the reaction mechanism to study the effect of having the conjugated aromatic moiety (BIAN-NHC) in the backbone of the complex. The newly synthesized BIAN-NHC Ru-complex shows comparable catalytic activities to the commercially available second generation Ru catalyst HG2. The recycled complex was reused for up to eight reaction cycles for the RCM of N,N-diallyl tosylamine affording a high average isolated yield, with lower levels of Ru contamination in the final product.[Figure Presented]

AB - Ruthenium catalyzed ring closing metathesis (RCM) and ring opening metathesis polymerization (ROMP) reactions using a supported bis(arylimino)acenaphthene N-heterocyclic carbene (BIAN-NHC) complex have been reported. The BIAN-NHC Ru-complex exhibits excellent catalytic activity and tolerates a wide range of substrates at low catalyst loadings. DFT calculations were also carried out on some selected key intermediates in the reaction mechanism to study the effect of having the conjugated aromatic moiety (BIAN-NHC) in the backbone of the complex. The newly synthesized BIAN-NHC Ru-complex shows comparable catalytic activities to the commercially available second generation Ru catalyst HG2. The recycled complex was reused for up to eight reaction cycles for the RCM of N,N-diallyl tosylamine affording a high average isolated yield, with lower levels of Ru contamination in the final product.[Figure Presented]

KW - Acenaphthenequinone

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KW - Ring opening metathesis polymerization

KW - Supported BIAN-NHC ruthenium complex

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