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Volumn 128, Issue 40, 2006, Pages 13261-13267

A new concept for the noncovalent binding of a ruthenium-based olefin metathesis catalyst to polymeric phases: Preparation of a catalyst on Raschig rings

Author keywords

[No Author keywords available]

Indexed keywords

GLASS POLYMER COMPOSITES; LIGANDS; METATHESIS CATALYST; RASCHIG RINGS;

EID: 33749523396     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063561k     Document Type: Article
Times cited : (150)

References (90)
  • 7
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    • For approaches where ruthenium impurities are removed by addition of various scavengers, see (a) Maynard, H. D.; Grubbs, R. H. Tetrahedron Lett. 2000, 40, 4137-4140.
    • (2000) Tetrahedron Lett. , vol.40 , pp. 4137-4140
    • Maynard, H.D.1    Grubbs, R.H.2
  • 10
    • 33749531163 scopus 로고    scopus 로고
    • note
    • (d) For a recent example of use of biphasic extraction of ruthenium remains in preparation of hepatitis C antiviral agent BILN 2061, see WO 2004/089974 A1 (2004, Boehringer Ingelheim International GmbH),
  • 51
    • 0012834678 scopus 로고    scopus 로고
    • Angew. Chem. 2002, 114, 4210-4212.
    • (2002) Angew. Chem. , vol.114 , pp. 4210-4212
  • 53
    • 33749516395 scopus 로고    scopus 로고
    • Boehringer Ingelheim International, U.S. Patent 6,867,303, 2005
    • (b) Grela K. Boehringer Ingelheim International, U.S. Patent 6,867,303, 2005. For applications of catalyst 6a and 6b,
    • Grela, K.1
  • 59
    • 33749534627 scopus 로고    scopus 로고
    • WO 2004/089974 A1, Boehringer Ingelheim International GmbH, 2004
    • (h) For a recent application in the synthesis of hepatitis C antiviral agent Ciluprevir (BILN 2061), see WO 2004/089974 A1, Boehringer Ingelheim International GmbH, 2004.
  • 62
    • 33749533384 scopus 로고    scopus 로고
    • Ph.D. Thesis, Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland
    • (a) Michrowska, A. Ph.D. Thesis, Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland, 2006.
    • (2006)
    • Michrowska, A.1
  • 66
    • 0031317101 scopus 로고    scopus 로고
    • and references therein
    • Hodge, P. Chem. Soc. Rev. 1997, 26, 417-424 and references therein.
    • (1997) Chem. Soc. Rev. , vol.26 , pp. 417-424
    • Hodge, P.1
  • 68
    • 33749523145 scopus 로고    scopus 로고
    • note
    • Alternate immobilization procedures relied on mixing catalyst 4 and ligand 9 (1:1) in the presence of cationic exchange resins to reduce leaching during RCM by trapping the active Ru species by the ligand. This procedure did not give improved results: 1st run 98%, 2nd run 82%, 3rd run 45%, 4th run 38%, 5th run 8%.
  • 73
    • 33749515386 scopus 로고    scopus 로고
    • note
    • This aspect is of particular importance when continuous flow processes are envisaged.
  • 75
    • 33749510422 scopus 로고    scopus 로고
    • note
    • 2O, and methanol. Then fresh catalyst 7 was loaded as described above and the "recharged" ring was used in the next cycle of metathesis. This experiment gave the following results: Initial catalyst, loading 3.0 μmol/ring, conversion 99%; 1st recharging, loading 3.0 μmol/ring, conversion 87%; 2nd recharging, loading 3.0 μmol/ring, conversion >99%; 3rd recharging, loading 2.8 μmol/ring, conversion 99%. See the Supporting Information for details.
  • 76
    • 33749527840 scopus 로고    scopus 로고
    • note
    • For high-throughput experiments described in Table 1 the Radleys 12 Place Heated Carousel Reaction Station (www.radleys.com) was used.
  • 86
    • 33749514909 scopus 로고    scopus 로고
    • note
    • Interestingly, in the case of 5 immobilized on polyvinyl pyridine, exclusive C-C double bond isomerization instead of CM was observed for this substrate: ref 15.
  • 89
    • 33749515566 scopus 로고    scopus 로고
    • unpublished results
    • The high activity of catalyst 7C has also been confirmed at Solvay GmbH by its application in CM of allylated steroids with α,β-unsaturated partners: Messinger, J.; Schön, U.; Mennecke, K.; Harmrohlf, K.; Kirschning, A. unpublished results.
    • Messinger, J.1    Schön, U.2    Mennecke, K.3    Harmrohlf, K.4    Kirschning, A.5
  • 90
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    • It has been recently demonstrated that free Ru carbene intermediates in solution can be scavenged by monolithic sol-gel glass-bound styrene ether ligands prior to the onset of competing transition metal decomposition. See Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4510-4517.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 4510-4517
    • Kingsbury, J.S.1    Hoveyda, A.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.