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Volumn , Issue 39, 2007, Pages 4056-4058

Consecutive palladium-catalyzed Hiyama-Heck reactions in aqueous media under ligand-free conditions

Author keywords

[No Author keywords available]

Indexed keywords

ARYL BROMIDE; BROMINE DERIVATIVE; ETHYLENE DERIVATIVE; LIGAND; MACROGOL; PALLADIUM; PALLADIUM ACETATE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG; WATER;

EID: 34948825887     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b707583a     Document Type: Article
Times cited : (50)

References (46)
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    • S. Bräse and A. de Meijere, in Metal-Catalyzed Cross-Coupling Reactions, ed., A. de Meijere, and, F. Diederich,, Wiley-VCH, Weinheim, 2nd edn, 2004, ch. 5
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    • Classical non-catalytic methods such as the Wittig or Horner-Wadsworth-Emmons reaction usually afford poor control over the (E) or (Z) configuration of the C-C double bonds. Catalytic methods for the synthesis of stilbenes have been recently reviewed:
    • N. S. C. R. Kumar I. V. P. Raj A. Sudalai J. Mol. Catal. A: Chem. 2007 269 218 224
    • (2007) J. Mol. Catal. A: Chem. , vol.269 , pp. 218-224
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  • 38
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    • Asymmetric 1,2-diarylethenes are also prepared by titanium-catalyzed McMurry coupling of aldehydes and ketones or by ruthenium-catalyzed cross-metathesis of vinylarenes, but the first procedure suffers from poor tolerance to functional groups and the second from low selectivities. See, for example:
    • K. Ferré-Filmon L. Delaude A. Demonceau A. F. Noels Coord. Chem. Rev. 2004 248 2323 2336
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  • 41
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    • 2Ar* (Ar* = 3,4-[18-crown-6]-phenyl) produced comparable results In contrast with our observations that short reaction times are key in the efficient synthesis of vinyl derivatives, high yields of 4-vinylacetophenone after 20 h of reaction at 120°C have been reported during the course of our work by Alacid and Nájera using tetrabutylammonium bromide (TBAB) as a nanoparticle stabilizer:
    • T. Jeffery B. Ferber Tetrahedron Lett. 2003 44 193 197
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    • Jeffery, T.1    Ferber, B.2
  • 42
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    • Poly(ethylene glycol) (PEG), pure or as a co-solvent, is an efficient medium for palladium-catalyzed coupling reactions.
    • E. Alacid C. Nájera Adv. Synth. Catal. 2006 348 2085 2091
    • (2006) Adv. Synth. Catal. , vol.348 , pp. 2085-2091
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    • See, for example, the experimental procedures described in the ESI for (E)-1,2-bis-[4-carboxyphenyl]ethene and (E)-1,2-bis-(3-quinolyl)ethene. Carboxy derivatives, which are water-soluble in their basic form, precipitate upon neutralization of the basic solution
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.