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Volumn 27, Issue 13, 2008, Pages 3187-3195

Unusual selectivity-determining factors in the phosphine-free heck arylation of allyl ethers

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; BROMINE COMPOUNDS; ORGANIC COMPOUNDS; PALLADIUM; PHOSPHORUS COMPOUNDS;

EID: 47949089113     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800114a     Document Type: Article
Times cited : (32)

References (65)
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    • 2 as precatalyst, see: (a) Bouquillon, S.; Ganchegui, B.; Estrinc, B.; Hénin, F.; Muzart, J. J. Organomet. Chem. 2001, 634, 153-156.
  • 19
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    • For the reaction of allyl alcohol with iodobenzene using palladium on porous glass, see
    • For the reaction of allyl alcohol with iodobenzene using palladium on porous glass, see: Li, J.; Mau, A. W.-H.; Strauss, C. R. Chem. Commun. 1997, 1275-1276.
    • (1997) Chem. Commun , pp. 1275-1276
    • Li, J.1    Mau, A.W.-H.2    Strauss, C.R.3
  • 20
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    • For the reaction in aqueous medium, see: a
    • For the reaction in aqueous medium, see: (a) Villemin, D.; Nechab, B. J. Chem. Res. 2000, 429-431.
    • (2000) J. Chem. Res , pp. 429-431
    • Villemin, D.1    Nechab, B.2
  • 24
    • 16244407390 scopus 로고    scopus 로고
    • For a recent review on the palladium-catalyzed reactions of alcohols, see
    • For a recent review on the palladium-catalyzed reactions of alcohols, see: Muzart, J. Tetrahedron 2005, 61, 4179-4212.
    • (2005) Tetrahedron , vol.61 , pp. 4179-4212
    • Muzart, J.1
  • 26
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    • Kang, S.-K.; Lee, H.-W.; Jang, S.-B.; Kim, T.-H.; Pyun, S.-J J. Org. Chem. 1996, 61, 2604-2605. See also
    • (a) Kang, S.-K.; Lee, H.-W.; Jang, S.-B.; Kim, T.-H.; Pyun, S.-J J. Org. Chem. 1996, 61, 2604-2605. See also
  • 32
    • 34547179974 scopus 로고    scopus 로고
    • Very recently, the same type of reaction was shown to be catalyzed by a heterogeneous palladium complex: Noel, S.; Lou, C.; Pinel, C.; Djakovitch, L. Adv. Synth. Catal. 2007, 349, 1128-1140.
    • Very recently, the same type of reaction was shown to be catalyzed by a heterogeneous palladium complex: Noel, S.; Lou, C.; Pinel, C.; Djakovitch, L. Adv. Synth. Catal. 2007, 349, 1128-1140.
  • 33
    • 0038106766 scopus 로고    scopus 로고
    • For recent reviews on the palladium-catalyzed oxidation of alcohols, see: a
    • For recent reviews on the palladium-catalyzed oxidation of alcohols, see: (a) Muzart, J. Tetrahedron 2003, 59, 5789-5816.
    • (2003) Tetrahedron , vol.59 , pp. 5789-5816
    • Muzart, J.1
  • 34
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    • 2 alcohol was prepared according to the method described by: Schuetz, R. D.; Millard, F. W. J. Org. Chem. 1959, 24, 297-300.
    • 2 alcohol was prepared according to the method described by: Schuetz, R. D.; Millard, F. W. J. Org. Chem. 1959, 24, 297-300.
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    • Compound 12j was prepared via selective hydrogenation of the tetrahydropyranyl derivative of 3-phenyl-2-propyn-1-ol according to the method described by: (a) Denis, J.-N.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46-50.
    • Compound 12j was prepared via selective hydrogenation of the tetrahydropyranyl derivative of 3-phenyl-2-propyn-1-ol according to the method described by: (a) Denis, J.-N.; Greene, A. E.; Serra, A. A.; Luche, M.-J. J. Org. Chem. 1986, 51, 46-50.
  • 50
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    • Ahlquist, M.; Fristrup, P.; Tanner, D.; Norrby, P.-O. Organometallics 2006, 25, 20662073.
    • (a) Ahlquist, M.; Fristrup, P.; Tanner, D.; Norrby, P.-O. Organometallics 2006, 25, 20662073.
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    • 3. For each complex investigated, we verify that this replacement does not produce any nonphysical hydrogen bonds.
    • 3. For each complex investigated, we verify that this replacement does not produce any nonphysical hydrogen bonds.
  • 55
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    • It has recently been suggested that under base-free, stoichiometric conditions, the carbopalladation step could become reversible: Amatore, C.; Godin, B.; Jutand, A.; Lemaître, F. Organometallics 2007, 26, 17571761. In the absence of a base-induced forward reaction, the barrier to the reverse reaction calculated herein would not be insurmountable.
    • It has recently been suggested that under base-free, stoichiometric conditions, the carbopalladation step could become reversible: Amatore, C.; Godin, B.; Jutand, A.; Lemaître, F. Organometallics 2007, 26, 17571761. In the absence of a base-induced forward reaction, the barrier to the reverse reaction calculated herein would not be insurmountable.
  • 59
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.