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Volumn 5, Issue 21, 2003, Pages 3803-3805

Palladium-Catalyzed Cross-Coupling of Acetates of Baylis-Hillman Adducts and Potassium Organotrifluoroborates

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; BORIC ACID; BORON; METHANOL; PALLADIUM; POTASSIUM; SODIUM CHLORIDE; SOLVENT;

EID: 0242628820     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0351798     Document Type: Article
Times cited : (94)

References (37)
  • 30
    • 0242427870 scopus 로고    scopus 로고
    • note
    • Isomer 4 was isolated in 18% yield for the aliphatic Baylis-Hillman reagent (Table 1, entry 4).
  • 35
    • 0037195743 scopus 로고    scopus 로고
    • Similar selectivity was observed in the Suzuki cross-coupling of potassium alkenyltrifluoroborates: Molander, G. A.; Bernardi, C. R. J. Org. Chem. 2002, 67, 8424.
    • (2002) J. Org. Chem. , vol.67 , pp. 8424
    • Molander, G.A.1    Bernardi, C.R.2
  • 36
    • 0034600318 scopus 로고    scopus 로고
    • It is interesting to note that trifluoroborate reagents have been shown to be ineffective in Suzuki coupling reactions with certain catalyst systems. See: Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4020
    • Littke, A.F.1    Dai, C.2    Fu, G.C.3
  • 37
    • 0242511317 scopus 로고    scopus 로고
    • note
    • 2 is added to a solution of potassium organotrifluoroborate salt 2 (1 mmol) in methanol (5 mL) at 0°C under a nitrogen atmosphere. The reaction mixture is allowed to stir at room temperaure until completion (TLC monitoring). The mixture is then diluted with diethyl ether (10 mL) and filtered to remove solids. The solvent is removed under reduced pressure and the product purified by chromatography (silica gel) to afford analytically pure product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.