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Volumn 4, Issue 12, 2012, Pages 2020-2025

Clean, convenient, high-yield access to second-generation ru metathesis catalysts from commercially available precursors

Author keywords

Homogeneous catalysis; Metathesis; N heterocyclic carbene; Ruthenium; Scavenger

Indexed keywords

EXCHANGE RESIN; HOMOGENEOUS CATALYSIS; ISOLATED YIELD; LIGAND EXCHANGES; METATHESIS; METATHESIS CATALYSTS; N-HETEROCYCLIC CARBENES; OLEFIN METATHESIS; RUTHENIUM CATALYSTS; SCAVENGER;

EID: 84870476379     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200540     Document Type: Article
Times cited : (26)

References (46)
  • 13
    • 84870449272 scopus 로고    scopus 로고
    • Trnka, Grubbs and co-workers observed small amounts of hydride species after washing the crude product with MeOH (see ref.[9]). This is unlikely to be due to reaction of GII with methanol, which is slow at room temperature. (See:
    • Trnka, Grubbs and co-workers observed small amounts of hydride species after washing the crude product with MeOH (see ref.[9]). This is unlikely to be due to reaction of GII with methanol, which is slow at room temperature. (See:
  • 15
    • 61849144288 scopus 로고    scopus 로고
    • Methoxide formed insitu may be a more likely culprit: see ref.[12].
    • N. J. Beach, J. M. Blacquiere, S. D. Drouin, D. E. Fogg, Organometallics 2009, 28, 441-447). Methoxide formed insitu may be a more likely culprit: see ref.[12].
    • (2009) Organometallics , vol.28 , pp. 441-447
    • Beach, N.J.1    Blacquiere, J.M.2    Drouin, S.D.3    Fogg, D.E.4
  • 23
    • 84870457063 scopus 로고    scopus 로고
    • 2. However, competing hydrolysis of the carbene (see main text) may complicate stoichiometric control in use of this species to synthesize second-generation metathesis catalysts.
    • 2. However, competing hydrolysis of the carbene (see main text) may complicate stoichiometric control in use of this species to synthesize second-generation metathesis catalysts.
  • 26
    • 84870440481 scopus 로고    scopus 로고
    • 2IMes can be stored up to 4.5months (to date) with no decomposition, when kept in the glovebox at -35°C in a taped screw-cap vial. The thermal stability of the free carbene described in the main text suggests that storage at room temperature should be equally successful, and more convenient.
    • 2IMes can be stored up to 4.5months (to date) with no decomposition, when kept in the glovebox at -35°C in a taped screw-cap vial. The thermal stability of the free carbene described in the main text suggests that storage at room temperature should be equally successful, and more convenient.
  • 36
    • 84870452566 scopus 로고    scopus 로고
    • Note
    • Trace water trapped in the pores is not removed by subjecting the resin in its dry form to heat and vacuum: instead, such pre-treatment must be followed by washing with dry THF to swell the resin and extract the water, prior to a second stage of heating under vacuum.
  • 38
    • 84870429388 scopus 로고    scopus 로고
    • 3 in preparative experiments.
    • 3 in preparative experiments.
  • 39
    • 84870404265 scopus 로고    scopus 로고
    • HI was prepared by cross-metathesis of GI with isopropoxystyrene in the presence of Amberlyst15 (50°C, THF, 2h), by analogy to the method used by Verpoort to prepare GII (ref.[32]). Yields were limited to ca. 90%, even on 8g scale, owing to losses incurred on washing out the styrene co-product.
    • HI was prepared by cross-metathesis of GI with isopropoxystyrene in the presence of Amberlyst15 (50°C, THF, 2h), by analogy to the method used by Verpoort to prepare GII (ref.[32]). Yields were limited to ca. 90%, even on 8g scale, owing to losses incurred on washing out the styrene co-product.
  • 40
    • 84870444709 scopus 로고    scopus 로고
    • 3 adduct remaining even after 12h.
    • 3 adduct remaining even after 12h.
  • 41
    • 84870434692 scopus 로고    scopus 로고
    • Synthesis of HII by the method of Scheme5b was originally described in the Verpoort patent (ref.[32]), but yields were not reported. Our synthesis was performed on 200mg GII, and improvements may therefore result from scaleup (though see ref.[37]).
    • Synthesis of HII by the method of Scheme5b was originally described in the Verpoort patent (ref.[32]), but yields were not reported. Our synthesis was performed on 200mg GII, and improvements may therefore result from scaleup (though see ref.[37]).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.