메뉴 건너뛰기




Volumn 349, Issue 11-12, 2007, Pages 1851-1857

An efficient and versatile approach for the immobilization of carbene precursors via copper-catalyzed [3+ 2]-cycloaddition and their catalytic application

Author keywords

Carbenes; Catalyst immobilization; Click chemistry; Organocatalysis; Redox esterification; Stetter reaction

Indexed keywords


EID: 34548414019     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700174     Document Type: Article
Times cited : (59)

References (65)
  • 2
    • 4143094833 scopus 로고    scopus 로고
    • special issue: Acc. Chem. Res. 2004, 37, 487-631;
    • b) special issue: Acc. Chem. Res. 2004, 37, 487-631;
  • 3
    • 34548446609 scopus 로고    scopus 로고
    • special issue: Adv. Synth. Catal. 2004, 346, 1007-1249;
    • c) special issue: Adv. Synth. Catal. 2004, 346, 1007-1249;
  • 12
    • 34250822311 scopus 로고    scopus 로고
    • for a related intramolecular Michael reaction, see: E. M. Phillips. M. Wadamoto, A. Chan, K. A. Scheidt, Angew. Chem. Int. Ed. 2007, 46, 3107-3110.
    • c) for a related intramolecular Michael reaction, see: E. M. Phillips. M. Wadamoto, A. Chan, K. A. Scheidt, Angew. Chem. Int. Ed. 2007, 46, 3107-3110.
  • 14
    • 0345732180 scopus 로고    scopus 로고
    • This is especially attractive to avoid elaborate separation techniques as, e.g, provided in continous-flow systems: a G. Jas, A. Kirschning, Chem. Eur. J. 2003, 9, 5708-5723;
    • This is especially attractive to avoid elaborate separation techniques as, e.g., provided in continous-flow systems: a) G. Jas, A. Kirschning, Chem. Eur. J. 2003, 9, 5708-5723;
  • 16
    • 33748257080 scopus 로고    scopus 로고
    • For a detailed discussion on this topic, see: a
    • For a detailed discussion on this topic, see: a) F. Cozzi, Adv. Synth. Catal. 2006, 348, 1367-1390;
    • (2006) Adv. Synth. Catal , vol.348 , pp. 1367-1390
    • Cozzi, F.1
  • 17
  • 21
    • 33846818369 scopus 로고    scopus 로고
    • In addition, several approaches for the immobilization of NHC ligands, mainly for Pd or Ru complexes, have been reported; a W. J. Sommer, M. Weck, Coord. Chem. Rev. 2007, 251, 860-873;
    • In addition, several approaches for the immobilization of NHC ligands, mainly for Pd or Ru complexes, have been reported; a) W. J. Sommer, M. Weck, Coord. Chem. Rev. 2007, 251, 860-873;
  • 27
    • 34548436820 scopus 로고    scopus 로고
    • [11]
    • [11]
  • 36
    • 33750447664 scopus 로고    scopus 로고
    • In general, the 1,2,3-triazole moiety shows high chemical inertness; for a rare, recent example of its use in Diels-Alder reactions under harsh conditions, see: A. Diáz-Ortiz, A. de Cózar, P. Prieto, A. de La Hoz, A. Moreno, Tetrahedron Lett. 2006, 47, 8761-8764.
    • In general, the 1,2,3-triazole moiety shows high chemical inertness; for a rare, recent example of its use in Diels-Alder reactions under harsh conditions, see: A. Diáz-Ortiz, A. de Cózar, P. Prieto, A. de La Hoz, A. Moreno, Tetrahedron Lett. 2006, 47, 8761-8764.
  • 44
    • 34548401488 scopus 로고    scopus 로고
    • As a result of such possible perturbations of the catalytic sites some erosion in enantioselectivites was observed
    • As a result of such possible perturbations of the catalytic sites some erosion in enantioselectivites was observed.
  • 46
    • 34248145294 scopus 로고    scopus 로고
    • For a combined Michael addition/cycloaddition immobilization approach in a packed-bed reactor, see: A. R. Bogdan, B. P. Mason, K. T. Sylvester, D. T. McQuade, Angew. Chem. Int. Ed. 2007, 46, 1698-1701.
    • For a combined Michael addition/cycloaddition immobilization approach in a packed-bed reactor, see: A. R. Bogdan, B. P. Mason, K. T. Sylvester, D. T. McQuade, Angew. Chem. Int. Ed. 2007, 46, 1698-1701.
  • 50
    • 15944397964 scopus 로고    scopus 로고
    • There are only few examples for the direct ligation of functional molecules bearing cationic groups via a CuAAC reaction: a H. A. Orgueira, D. Fokas, Y. Isome, P. C.-M. Chan, C. M. Baldino, Tetrahedron Lett. 2005, 46, 2911-2914;
    • There are only few examples for the direct ligation of functional molecules bearing cationic groups via a CuAAC reaction: a) H. A. Orgueira, D. Fokas, Y. Isome, P. C.-M. Chan, C. M. Baldino, Tetrahedron Lett. 2005, 46, 2911-2914;
  • 54
    • 20344388819 scopus 로고    scopus 로고
    • in this context see also: b S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. Int. Ed. 2005, 44, 3275-3279.
    • in this context see also: b) S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. Int. Ed. 2005, 44, 3275-3279.
  • 55
    • 34250883966 scopus 로고    scopus 로고
    • Mechanistic investigations of Straub also indicate the important role of protonation and deprotonation processes within the catalytic cycle subject to the acidity of the reaction medium: C. Nolte, P. Mayer, B. F. Straub, Angew. Chem. Int. Ed. 2007, 46, 2101-2103
    • Mechanistic investigations of Straub also indicate the important role of protonation and deprotonation processes within the catalytic cycle subject to the acidity of the reaction medium: C. Nolte, P. Mayer, B. F. Straub, Angew. Chem. Int. Ed. 2007, 46, 2101-2103.
  • 57
    • 18844424752 scopus 로고    scopus 로고
    • For a recent review see
    • For a recent review see: M. Christmann, Angew. Chem. Int. Ed. 2005, 44, 2632-2634.
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 2632-2634
    • Christmann, M.1
  • 61
    • 3242812738 scopus 로고    scopus 로고
    • Highly enantioselective triazolium-catalyzed formation of quarternary centers was developed by Rovis et al, M. S. Kerr, T. Rovis, J. Am. Chem. Soc. 2004, 126, 8876-8877; its racemic variant using commercially available thiazolium salts requires much higher catalyst loading and harsh reaction conditions 30 mol, 70°C, 24 h, see ref, 33b
    • [33b]
  • 62
    • 34548384168 scopus 로고    scopus 로고
    • In all cases, the purity of the isolated chromanones was > 95, 1H NMR, See Supporting Information
    • 1H NMR). See Supporting Information.
  • 63
    • 33846807717 scopus 로고    scopus 로고
    • The use of ionic liquids as solvent for this microwavepromoted reaction might be an example of a non-innocent ionic liquid: a S. Chowdhury, R. S. Mohan, J. L. Scott, Tetrahedron 2007, 63, 2363-2389;
    • The use of ionic liquids as solvent for this microwavepromoted reaction might be an example of a "non-innocent" ionic liquid: a) S. Chowdhury, R. S. Mohan, J. L. Scott, Tetrahedron 2007, 63, 2363-2389;
  • 65


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.