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Synlett
Volumn , Issue 6, 2009, Pages 973-977
Palladium-catalyzed arylation of the THP derivative of (Z)-2-butene-1,4- diol with arenediazonium salts and the synthesis of β-aryl-γ- butyrolactones
Author keywords

Allylic alcohols; Arenediazonium salts; Mizoroki heck reaction; Palladium; Tetrahydrofurans
Indexed keywords

BUTYROLACTONE; DIAZONIUM COMPOUND; PALLADIUM; TETRAHYDROFURAN DERIVATIVE;
EID: 63849190929     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087959     Document Type: Article
Times cited : (18)
References (50)
  • 24
    • 63849231426 scopus 로고    scopus 로고
    • Hu, R.-H.; Piu, X.-P.; Cai, M.-Z. Jiangxi Shifan Daxue Xuebao, Ziran Kexueban 2001, 25, 246; Chem. Abstr. 2001, 136, 355024.
    • (b) Hu, R.-H.; Piu, X.-P.; Cai, M.-Z. Jiangxi Shifan Daxue Xuebao, Ziran Kexueban 2001, 25, 246; Chem. Abstr. 2001, 136, 355024.
  • 27
    • 34249104674 scopus 로고    scopus 로고
    • For an excellent recent review on the palladium chemistry of arenediazonium salts, see
    • For an excellent recent review on the palladium chemistry of arenediazonium salts, see: Roglans, A.; Pla-Quintana, A.; Moreno-Mañas, M. Chem. Rev. 2006, 106, 4622.
    • (2006) Chem. Rev , vol.106 , pp. 4622
    • Roglans, A.1    Pla-Quintana, A.2    Moreno-Mañas, M.3
  • 30
    • 16244407390 scopus 로고    scopus 로고
    • For some recent reviews on the palladium-catalyzed synthesis of heterocycles from unsaturated alcohols, see: (a) Muzart, J. Tetrahedron 2005, 61, 4179
    • For some recent reviews on the palladium-catalyzed synthesis of heterocycles from unsaturated alcohols, see: (a) Muzart, J. Tetrahedron 2005, 61, 4179.
  • 37
    • 0001781032 scopus 로고    scopus 로고
    • Alternatively, as suggested by one of the referees, 5b might arise from 4b via proton loss and addition of MeOH to the resultant dihydrofuran (although no evidence was attained of the formation of such an intermediate). The tendency of furanols 1 to dehydrate upon distillation has been described: (a) Chalk, A. P.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. In the case of formation of the dihydrofuran intermediate, the addition of MeOH to the carbon-carbon double bond might occur via an acid-catalyzed process:
    • Alternatively, as suggested by one of the referees, 5b might arise from 4b via proton loss and addition of MeOH to the resultant dihydrofuran (although no evidence was attained of the formation of such an intermediate). The tendency of furanols 1 to dehydrate upon distillation has been described: (a) Chalk, A. P.; Magennis, S. A. J. Org. Chem. 1976, 41, 273. In the case of formation of the dihydrofuran intermediate, the addition of MeOH to the carbon-carbon double bond might occur via an acid-catalyzed process:
  • 38
    • 0842349047 scopus 로고    scopus 로고
    • Palladium-catalyzed hydroalkoxylation of carbon-carbon double bonds has also been reported
    • (b) Wabnitz, T. C; Yu, J.-Q.; Spencer, J. B. Chem. Eur. J. 2004, 10, 484. Palladium-catalyzed hydroalkoxylation of carbon-carbon double bonds has also been reported:
    • (2004) Chem. Eur. J , vol.10 , pp. 484
    • Wabnitz, T.C.1    Yu, J.-Q.2    Spencer, J.B.3
  • 40
    • 15444376499 scopus 로고    scopus 로고
    • Matsukawa, Y.;Mizukado, J.; Quan, H.; Tamura, M.; Sekiya, A. Angew. Chem. Int. Ed. 2005, 44, 1128; see also ref. 6a,b.
    • (d) Matsukawa, Y.;Mizukado, J.; Quan, H.; Tamura, M.; Sekiya, A. Angew. Chem. Int. Ed. 2005, 44, 1128; see also ref. 6a,b.
  • 49
    • 63849219246 scopus 로고    scopus 로고
    • Preparation of 4- Aryl-2-methoxytetrahydrofuran (5) via Palladium-Catalyzed Reaction of Arenediazonium Tetrafluoroborates 2 with the THP Derivative of (Z)-2- Buten-l,4-diol (6, Typical Procedure To a stirred solution of 6 (128.2 mg, 0.50 mmol) and Pd(OAc)2 (5.6 mg, 0.025 mmol) in anhyd MeOH (4.0 mL, 2a (221.9 mg, 1.0 mmol) was added at r.t. under argon. The reaction mixture was warmed at 35 °C and stirred for 1 h (the reactor was protected from light with aluminium film, After cooling, the reaction mixture was diluted with Et2O, washed with a sat. NaHCO3 solution, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel [n-hexane-EtOAc, 75:25 (v/v, to afford 75.2 mg (72% yield) of 5a as an approximately 60:40 diastereomeric mixture. The cis-isomer was isolated and characterized. Oil. IR neat, 2940
    • +], 177 (22), 147 (68).
  • 50
    • 63849168755 scopus 로고    scopus 로고
    • Preparation of β-Aryl-γ-butyrolactones 13 from Arenediazonium Tetrafluoroborates 2 and the THP Derivative of (Z)-2-Buten-l,4-diol (6) via a Sequential Palladium-Catalyzed Arylation-Cyclization-Oxidation Protocol, Typical Procedure To a stirred solution of 6 (128.2 mg, 0.50 mmol) and Pd(OAc)2 (5.6 mg, 0.025 mmol) in anhyd MeOH (4.0 mL, 2b (250.0 mg, 1.0 mmol) was added at r.t. under argon. The reaction mixture was warmed at 35 °C and stirred for 45 min (the reactor was protected from light with aluminium film, After this time, the reaction mixture was diluted with Et2O, washed with a sat. NaHCO3 solution, dried overNa2SP4, and concentrated under reduced pressure. The residue was filtrated through a short bed of SiO2 and concentrated under reduced pressure. The crude was dissolved in CH2C12 (3 mL) and MCPBA 123.3 mg, 0.5 mmol; a commercially available 70% MCPBA
    • +], 162 (59), 131(100), 77(89).

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