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Volumn , Issue 16, 2008, Pages 2540-2546

Iron/copper-cocatalyzed ullmann N,O-arylation using FeCl3, CuO, and rac-1,1′-Binaphthyl-2,2′-diol

Author keywords

Copper; Cross coupling; Iron; N arylation; O arylation

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALIPHATIC COMPOUND; AROMATIC AMINE; BROMINE DERIVATIVE; COPPER; COPPER OXIDE; FERRIC CHLORIDE; IODINE DERIVATIVE; IRON; NITROGEN; OXIDE; OXYGEN; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 54149092549     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078214     Document Type: Article
Times cited : (35)

References (58)
  • 35
    • 0030700314 scopus 로고    scopus 로고
    • See some recent reports for O-arylation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
    • See some recent reports for O-arylation: (a) Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539.
  • 42
    • 0031871453 scopus 로고    scopus 로고
    • For recent work dealing with iron-mediated arylations concerning C-C bond formation, see: a
    • For recent work dealing with iron-mediated arylations concerning C-C bond formation, see: (a) Cahiez, G.; Avedissian, H. Synthesis 1998, 1199.
    • (1998) Synthesis , pp. 1199
    • Cahiez, G.1    Avedissian, H.2
  • 57
    • 54149099710 scopus 로고    scopus 로고
    • General Procedure A: Coupling of Aryl Halides with Amines A flask was charged with FeCl3 (16 mg, 0.1 mmol, CuO (8 mg, 0.1 mmol, Cs2CO3 (651 mg, 2 mmol, BINOL (57 mg, 0.2 mmol, and any remaining solids (amine and/or aryl halide, The flask was evacuated and backfilled with nitrogen (this procedure was repeated five times, Aryl halide (1 mmol, if liquid, amine (1.2 mmol, if liquid, and DMF (2 mL) were added to the flask under nitrogen atmosphere. The mixture was allowed to stir under nitrogen atmosphere at the shown temperature for the indicated period of time in the text (see Tables 1 and 2, After cooling to r.t, the mixture was diluted with CH2Cl2 (ca. 20 mL, the solution was filtered, and the filter cake was further washed with CH2Cl2 (ca. 5 mL, The filtrate was washed with 1 M NaOH (ca. 10 mL, The combined aqueous phase was extracted with CH2Cl2 2 x 10 mL, Organic l
    • +].
  • 58
    • 54149091941 scopus 로고    scopus 로고
    • General Procedure B: Coupling of Aryl Halides with Phenols A flask was charged with FeCl3 (16 mg, 0.1 mmol, CuO (8 mg, 0.1 mmol, Cs2CO3 (651 mg, 2 mmol, 1,1′-binaphthyl-2,2′- diol (57 mg, 0.2 mmol, and any remaining solids (phenol and/or aryl halide, The flask was evacuated and backfilled with nitrogen (this procedure was repeated five times, Aryl halide (1 mmol, if liquid, phenol (1.2 mmol, if liquid, and DMF (2 mL) were added to the flask under nitrogen atmosphere. The flask mixture was allowed to stir under nitrogen atmosphere at the shown temperature for the indicated period of time in the text (see Table 3, After cooling to r.t, the mixture was diluted with CH2Cl2 (ca. 20 mL, the solution was filtered, and the filter cake was further washed with CH2Cl2 ca. 5 mL, The solvent of the filtrate was removed with the aid of a rotary evaporator, and the residue was purified by colu
    • +].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.