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Volumn 126, Issue 46, 2004, Pages 15195-15201

Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHLORINE COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); TRANSITION METALS;

EID: 9344240844     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045349r     Document Type: Article
Times cited : (531)

References (66)
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    • For other catalysts based on phosphine ligands, see, for example: (a) Shen, W. Tetrahedron Lett. 1997, 38, 5575.
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    • Shen, W.1
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    • For other catalysts based on NHC ligands, see, for example; (a) Zhang, C.; Trudell, M. L. Tetrahedron Lett. 2000, 41, 595.
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    • Zhang, C.1    Trudell, M.L.2
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    • For excellent reviews on the use of NHC ligands in catalysis, see: (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1291.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1291
    • Herrmann, W.A.1
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    • note
    • Subsequently, two other catalyst systems have been reported for Suzuki-Miyaura reactions of sterically hindered aryl chlorides at ambient temperature, the latter being exceptionally practical and general: refs 8e and 4d. However, none of these systems has been reported to allow the successful formation of tetraortho-substituted biaryls from aryl chlorides.
  • 45
    • 9344266649 scopus 로고    scopus 로고
    • ref 5b
    • The importance of monoligated Pd(0) complexes as catalytically active species in Suzuki-Miyaura cross-coupling has been proposed. See, for example: (a) ref 5b;
  • 46
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    • ref 6e
    • (b) ref 6e;
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    • For the successful application of an interesting sterically demanding NHC ligand in a difficult Sonogashira coupling, see: (d) Ma, Y.; Song, C.; Jiang, W.; Wu, Q.; Wang, Y.; Liu, X.; Andrus, M. B. Org. Lett. 2003, 5, 3317.
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    • (c) Abiko, A.; Masamune, S. Tetrahedron Lett. 1992, 33, 5517). This method allows the convenient synthesis of large gram quantities of amino alcohol.
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    • note
    • 2 (0.17 M) at 40 °C leads to the smooth formation of IMes-HOTf in 83%. Related systems react equally well.
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    • 17th November
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    • note
    • Commercial sources provide boronic acids of substantially different dryness. Recrystallization may be advisable in some cases.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.