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Volumn 349, Issue 17-18, 2007, Pages 2572-2584

Arylation of allyl alcohols in organic and aqueous media catalyzed by oxime-derived palladacycles: Synthesis of β-arylated carbonyl compounds

Author keywords

Allyl alcohols; Carbonyl compounds; Heck reaction; Palladacycles; Polymeric reagents

Indexed keywords


EID: 37349049611     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700301     Document Type: Article
Times cited : (56)

References (69)
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    • For other applications of palladacycles 12 and 13 in organic synthesis, see: a biaryl sulfones by Suzuki reaction: A. Costa, C. Nájera, J. M. Sansano, J. Org. Chem. 2002, 67, 5216-5225;
    • For other applications of palladacycles 12 and 13 in organic synthesis, see: a) biaryl sulfones by Suzuki reaction: A. Costa, C. Nájera, J. M. Sansano, J. Org. Chem. 2002, 67, 5216-5225;
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    • Heck multiple vinylation of tribenzotriquinacenes and fenestrindanes: X.-P. Cao, D. Barth, D. Kuck, Eur. J. Org. Chem. 2005, 3482-3488.
    • c) Heck multiple vinylation of tribenzotriquinacenes and fenestrindanes: X.-P. Cao, D. Barth, D. Kuck, Eur. J. Org. Chem. 2005, 3482-3488.
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    • For applications of complex 14 and related Kaiser oxime resin 15 in Heck reactions with acrylic systems and styrenes, see: E. Alacid, C. Nájera, Synlett 2006, 2959-2963.
    • For applications of complex 14 and related Kaiser oxime resin 15 in Heck reactions with acrylic systems and styrenes, see: E. Alacid, C. Nájera, Synlett 2006, 2959-2963.
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    • This reaction was firstly studied by Heck[19a] and Chalk [30] simultaneously using Pd(OAc)2 1 mol , and triethylamine as base in acetonitrile
    • 2 (1 mol %) and triethylamine as base in acetonitrile.
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    • 3: H. Zhao, M.-Z. Cai, R.-H. Hu, C.-S. Song, Synth. Commun. 2001, 31, 3665-3669.
    • 3: H. Zhao, M.-Z. Cai, R.-H. Hu, C.-S. Song, Synth. Commun. 2001, 31, 3665-3669.
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    • The temperature of the reaction mixture inside the vessel was monitored using a calibrated infrared temperature control under the reaction vessel
    • The temperature of the reaction mixture inside the vessel was monitored using a calibrated infrared temperature control under the reaction vessel.
  • 62
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    • It is known that TBAB stabilizes colloidal palladium nanoparticles acting as catalysts in cross-coupling reactions: R. T. Reetz, E. Westermann, Angew. Chem. Int. Ed. 2000, 39, 165-168
    • It is known that TBAB stabilizes colloidal palladium nanoparticles acting as catalysts in cross-coupling reactions: R. T. Reetz, E. Westermann, Angew. Chem. Int. Ed. 2000, 39, 165-168.
  • 64
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    • This type of arylation has been studied with allyl alcohol (1c) and 2-iodoaniline in water with Pd(OAc)2 and 3,3′,3″- phosphinidyne tris(benzenesulfonic acid) trisodium salt (TPPTS) as ligand to give the corresponding 3-methylindol after a two-step process.[34
    • [34]
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    • For the synthesis of diene 21a by means of the Wittig reaction, see: R. Tamura, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1988, 53, 2723-2728.
    • For the synthesis of diene 21a by means of the Wittig reaction, see: R. Tamura, K. Saegusa, M. Kakihana, D. Oda, J. Org. Chem. 1988, 53, 2723-2728.
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    • For the synthesis of 1-aryl-3-methyl-1,3-dienes from methallyl(trimethyl) silane, see
    • For the synthesis of 1-aryl-3-methyl-1,3-dienes from methallyl(trimethyl) silane, see: S. R. Dubbaka, P. Vogel, Tetrahedron 2005, 61, 1523-1530.
    • (2005) Tetrahedron , vol.61 , pp. 1523-1530
    • Dubbaka, S.R.1    Vogel, P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.