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Volumn , Issue 15, 2007, Pages 2331-2336

Palladium-catalyzed couplings of heteroaryl amines with aryl halides using sodium phenolate as the stoichiometric base

Author keywords

Biaryl amine; C N bond forming; Heteroaryl amine; Palladium catalyzed; Sodium phenolate

Indexed keywords

AROMATIC AMINE; HALIDE; PALLADIUM; PHENOL DERIVATIVE; SODIUM;

EID: 34948866679     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985597     Document Type: Article
Times cited : (28)

References (27)
  • 12
    • 34948815819 scopus 로고    scopus 로고
    • At the time of this manuscript's preparation, a search via ACD and ACX failed to find any commercially available arylnonaflates
    • At the time of this manuscript's preparation, a search via ACD and ACX failed to find any commercially available arylnonaflates.
  • 18
    • 0033597748 scopus 로고    scopus 로고
    • For examples of NaOPh in Pd-catalyzed couplings of carbamates to aryl halides, see: (a) Hartwig, J. F, Kawatsura, M, Hauck, S. I, Shaughnessy, K. H, Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575
    • For examples of NaOPh in Pd-catalyzed couplings of carbamates to aryl halides, see: (a) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
  • 20
    • 34948908876 scopus 로고    scopus 로고
    • For the use of NaOPh in isoprene dimerization, see: Komatsu, A.; Akutagawa, S.; Someya, T. U 3859374, 1975.
    • (c) For the use of NaOPh in isoprene dimerization, see: Komatsu, A.; Akutagawa, S.; Someya, T. U 3859374, 1975.
  • 21
    • 33846563488 scopus 로고    scopus 로고
    • 3, see: (a) Shekhar, S.; Hartwig, J. F. Organometallics 2007, 26, 340.
    • 3, see: (a) Shekhar, S.; Hartwig, J. F. Organometallics 2007, 26, 340.
  • 23
    • 34948898793 scopus 로고    scopus 로고
    • All microwave reactions were conducted in a 2-5 mL Biotage Microwave Vial Kit with sealable cap (code no. 351521) using a magnetic stirbar. Microwave heating was performed with a single-mode cavity Emrys SmithCreator.
    • All microwave reactions were conducted in a 2-5 mL Biotage Microwave Vial Kit with sealable cap (code no. 351521) using a magnetic stirbar. Microwave heating was performed with a single-mode cavity Emrys SmithCreator.
  • 24
    • 34948897734 scopus 로고    scopus 로고
    • General Procedure for Compounds Shown in Table 3 A 2-5 mL Biotage microwave vial was charged with the aryl halide (1.10 mmol, sodium phenolate (191 mg, 1.65 mmol, Pd2(dba)3 (12.6 mg, 0.0137 mmol, 2.5 mol% of Pd, and Xantphos (19.1 mg, 0.0330 mmol, 3.0 mol, followed by degassed 1,4-dioxane (6.50 mL, The mixture was stirred while degassing with argon for 1 min. The heteroaryl amine (1.21 mmol) was added last, the vial was immediately capped and sealed, then heated at 80°C for 2 h. After cooling to r.t, the mixture was diluted with EtOAc (400 mL, washed with 1 N aq NaOH (3 x 100 mL) and brine (100 mL, dried over anhyd Na2SO4, filtered, and the solvent removed under vacuum. The resulting residue was purified over silica gel (12 g, hexanes-EtOAc) and the product was freeze-dried from MeCN-H2O to provide the pure product
    • 2O to provide the pure product.
  • 25
    • 0033531744 scopus 로고    scopus 로고
    • For studies on the scope and limitations of Pd-catalyzed formation of biarylethers from sodium phenolates, see: (a) Mann, G, Incarvito, C, Rheingold, A. L, Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224
    • For studies on the scope and limitations of Pd-catalyzed formation of biarylethers from sodium phenolates, see: (a) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.