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Volumn 53, Issue 46, 2012, Pages 6219-6222

Copper promoted Chan-Lam type O-arylation of oximes with arylboronic acids at room temperature

Author keywords

Cesium carbonate; Chan Lam; Copper acetate; Oxime ether; Phenylboronic acid

Indexed keywords

ARYLBORONIC ACID; ARYLOXIME; ARYLOXIME ETHER; BORONIC ACID DERIVATIVE; COPPER; ETHER DERIVATIVE; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84867562708     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.09.003     Document Type: Article
Times cited : (39)

References (72)
  • 52
    • 33644647605 scopus 로고    scopus 로고
    • Hall D. G. Ed.; Wiley-VCH: Weinheim, Chapter 5
    • Chan, D. M. T.; Lam, P. Y. S. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; pp 205-240. Chapter 5.
    • (2005) Boronic Acids , pp. 205-240
    • Chan, D.M.T.1    Lam, P.Y.S.2
  • 66
    • 85031176330 scopus 로고    scopus 로고
    • General procedure: To a mixture of acetophenone oxime (1a, 135 mg, 1 mmol), Cu(OAc)2 (100 mg, 0.5 mmol), Cs2CO3 (325 mg, 1 mmol), aryl boronic acid (2a, 242 mg, 2 mmol) and 4 ml of DMSO was added in open atmosphere in a 50 ml round bottom flask. The mixture was stirred at room temperature and the progress was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with dil. NH4Cl-H2O solution and extracted with ethyl acetate (3 -20 ml). Then the extract was washed with brine (2 -20 ml) and dried over Na2SO4 and evaporated on reduced pressure. Residue was purified by silica gel chromatography (ethyl acetate-hexane: 1:9) to obtained the desired products. Thin-layer chromatography was carried out with Merck silica gel 60F254 plates. Products were characterized by 1H NMR, 13C NMR, FTIR spectroscopy and Mass spectroscopy
    • General procedure: To a mixture of acetophenone oxime (1a, 135 mg, 1 mmol), Cu(OAc)2 (100 mg, 0.5 mmol), Cs2CO3 (325 mg, 1 mmol), aryl boronic acid (2a, 242 mg, 2 mmol) and 4 ml of DMSO was added in open atmosphere in a 50 ml round bottom flask. The mixture was stirred at room temperature and the progress was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with dil. NH4Cl-H2O solution and extracted with ethyl acetate (3 -20 ml). Then the extract was washed with brine (2 -20 ml) and dried over Na2SO4 and evaporated on reduced pressure. Residue was purified by silica gel chromatography (ethyl acetate-hexane: 1:9) to obtained the desired products. Thin-layer chromatography was carried out with Merck silica gel 60F254 plates. Products were characterized by 1H NMR, 13C NMR, FTIR spectroscopy and Mass spectroscopy.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.