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Volumn 10, Issue 18, 2008, Pages 3949-3952

Practical Heck-Mizoroki coupling protocol for challenging substrates mediated by an N-heterocyclic carbene-ligated palladacycle

Author keywords

[No Author keywords available]

Indexed keywords

CARBENE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; METHANE; ORGANOMETALLIC COMPOUND; PALLADIUM;

EID: 55949121369     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8012809     Document Type: Article
Times cited : (82)

References (52)
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    • (2004) Metal-catalyzed cross-coupling reactions
  • 6
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    • Recent examples: (a) Margolis, B. J.; Long, K. A.; Laird, D. L. T.; Ruble, J. C.; Pulley, S. R. J. Org. Chem. 2007, 72, 2232.
    • Recent examples: (a) Margolis, B. J.; Long, K. A.; Laird, D. L. T.; Ruble, J. C.; Pulley, S. R. J. Org. Chem. 2007, 72, 2232.
  • 26
    • 61349107736 scopus 로고    scopus 로고
    • Reviews and books: (a) N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Springer-Verlag: Berlin Heildergerg, 2007.
    • Reviews and books: (a) N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Springer-Verlag: Berlin Heildergerg, 2007.
  • 28
  • 35
    • 33845722103 scopus 로고    scopus 로고
    • While this work was in progress, a similar complex was reported independently: Cao, X.-H, Zheng, Y, Yu, H.-W, Shi, J.-C. J. Coord. Chem. 2007, 60, 207
    • While this work was in progress, a similar complex was reported independently: Cao, X.-H.; Zheng, Y.; Yu, H.-W.; Shi, J.-C. J. Coord. Chem. 2007, 60, 207.
  • 43
    • 0013308257 scopus 로고    scopus 로고
    • For 37: Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053.
    • (a) For 37: Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053.
  • 44
    • 61349157759 scopus 로고    scopus 로고
    • For 38: see ref 9b
    • (b) For 38: see ref 9b.
  • 45
    • 33745472389 scopus 로고    scopus 로고
    • For 39: O'Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem. - Eur. J. 2006, 12, 4743.
    • (c) For 39: O'Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem. - Eur. J. 2006, 12, 4743.
  • 46
    • 0037416262 scopus 로고    scopus 로고
    • For 40 and 41: Bedford, R. B.; Cazin, C. S. J.; Coles, S. J.; Gelbrich, T.; Horton, P. N.; Hursthouse, M. B.; Light, M. E. Organometallics 2003, 22, 987.
    • (d) For 40 and 41: Bedford, R. B.; Cazin, C. S. J.; Coles, S. J.; Gelbrich, T.; Horton, P. N.; Hursthouse, M. B.; Light, M. E. Organometallics 2003, 22, 987.
  • 47
    • 85170224352 scopus 로고    scopus 로고
    • 2]: Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989. This catalyst rapidly degraded upon dissolution in NMP and had to be weighed in as a solid.
    • 2]: Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989. This catalyst rapidly degraded upon dissolution in NMP and had to be weighed in as a solid.
  • 48
    • 0037020372 scopus 로고    scopus 로고
    • For 42: Schnyder, A.; Ingolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem., Int. Ed. 2002, 41, 3668.
    • (f) For 42: Schnyder, A.; Ingolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem., Int. Ed. 2002, 41, 3668.
  • 49
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    • For 43, 44: see ref 6a
    • (g) For 43, 44: see ref 6a.
  • 50
    • 34547230277 scopus 로고    scopus 로고
    • N-Methylimidazole-Pd complexes are also catalytically active in the Heck-Mizoroki reaction of bromoarenes at 1 mol % Pd. See: Haneda, S.; Ueba, C.; Eda, K.; Hayashi, M. Adv. Synth. Catal. 2007, 349, 833.
    • N-Methylimidazole-Pd complexes are also catalytically active in the Heck-Mizoroki reaction of bromoarenes at 1 mol % Pd. See: Haneda, S.; Ueba, C.; Eda, K.; Hayashi, M. Adv. Synth. Catal. 2007, 349, 833.
  • 51
    • 61349177391 scopus 로고    scopus 로고
    • 3P is much lower than IMes·HCl. Complex 40 is, therefore, also an excellent choice as a Heck-Mizoroki catalyst from a practical point of view: van der Schaaf, P. A, Kolly, R, Tinkl, M. PCT Int. Appl. WO 2003013723 2003
    • 3P is much lower than IMes·HCl. Complex 40 is, therefore, also an excellent choice as a Heck-Mizoroki catalyst from a practical point of view: van der Schaaf, P. A.; Kolly, R.; Tinkl, M. PCT Int. Appl. WO 2003013723 (2003).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.