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Volumn 47, Issue 17, 2006, Pages 2925-2928

The first palladium-catalyzed Sonogashira coupling of unactivated secondary alkyl bromides

Author keywords

Cross coupling; N heterocyclic carbene; Palladium; Secondary alkyl halide; Sonogashira coupling

Indexed keywords

1,2 DIAMINOCYCLOHEXANE; ALKYNE DERIVATIVE; BROMINE DERIVATIVE; CARBENE; CYCLOHEPTYL BROMIDE; HALIDE; LIGAND; PALLADIUM; UNCLASSIFIED DRUG;

EID: 33645243581     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.111     Document Type: Article
Times cited : (180)

References (44)
  • 26
    • 2442497333 scopus 로고    scopus 로고
    • For the Kumada-Corriu reaction of primary alkyl halides with alkynyl nucleophiles, see: L.-M. Yang, L.-F. Hunag, and T.-Y. Luh Org. Lett. 6 2004 1461
    • (2004) Org. Lett. , vol.6 , pp. 1461
    • Yang, L.-M.1    Hunag, L.-F.2    Luh, T.-Y.3
  • 27
    • 0004116546 scopus 로고
    • The uncatalyzed coupling of deprotonated alkynes with secondary alkyl halides is described in the following references, resulting in yields of up to 6%, 11% or 4%, respectively: J.M. Chong, and S. Wong Tetrahedron Lett. 27 1986 5445
    • (1986) Tetrahedron Lett. , vol.27 , pp. 5445
    • Chong, J.M.1    Wong, S.2
  • 32
    • 0001627662 scopus 로고    scopus 로고
    • For excellent reviews on the use of NHC ligands in catalysis, see: W.A. Herrmann Angew. Chem., Int. Ed. 41 2002 1291
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1291
    • Herrmann, W.A.1
  • 39
    • 33645225816 scopus 로고    scopus 로고
    • note
    • This is in contrast to our results in the Suzuki-Miyaura reaction, where IBiox12 was the optimal ligand system: Ref. 10b.
  • 40
    • 0037178121 scopus 로고    scopus 로고
    • The beneficial effect of diamine ligands on copper-catalyzed reactions has recently been explored by Buchwald: A. Klapars, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 124 2002 7421 and references cited therein
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 7421
    • Klapars, A.1    Huang, X.2    Buchwald, S.L.3
  • 42
    • 33645237581 scopus 로고    scopus 로고
    • Ref. 1a.
    • Ref. 1a.
  • 43
    • 33645233671 scopus 로고    scopus 로고
    • note
    • Due to the low polarity of the products, purification was rather tedious and in several cases multiple chromatographic steps were needed.
  • 44
    • 33645234197 scopus 로고    scopus 로고
    • note
    • 4 (20 mL) and concentrated under reduced pressure. After purification by flash chromatography (eluent: hexane or pentane/diethylether) the products were obtained as pale-yellow liquids.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.