• Title/Summary/Keyword: Aryl bromides

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Palladium Catalyzed Synthesis of Aryl Conjugated Enamides (팔라듐 촉매를 이용한 Aryl Conjugated Enamides의 합성)

  • Young Taik Hong;Jong Tae Lee;Cheol Mo Ryu;Kim, Jin Il
    • Journal of the Korean Chemical Society
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    • v.29 no.3
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    • pp.287-294
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    • 1985
  • Acrylamide, N-alkyl substituted acrylamides and N,N-diethylacrylamide were reacted with aryl bromides in the presence of triethylamine and palladium acetate-triorthotolyl phosphine catalyst to form the various substituted aryl conjugated enamides. These reactions proceeded selectively and (E)-isomer of aryl conjugated enamides was obtained. N-alkyl substituted acrylamides were more reactive than acrylamide or N,N-diethylacrylamide and gave high yields of vinylated products. Aryl bromides with electron withdrawing group showed good reactivity but aryl bromides with electron donating group showed poor reactivity or no reactivity for acrylamide or N,N-diethylacrylamide.

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Tris(2-methoxyphenyl)phosphine as a Highly Active Ligand for the Synthesis of Biaryls by Suzuki Coupling Reaction

  • Kang, Pill-Seong;Ko, Sung-Bo;Ko, Jang-Myoun;Park, Jeong-Ho
    • Bulletin of the Korean Chemical Society
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    • v.30 no.11
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    • pp.2697-2700
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    • 2009
  • A $Pd(OAc)_2/(o-MeOPh)_3P$ system has been developed for the catalytic Suzuki coupling of aryl bromides with arylboronic acids. Our catalyst system covers a broad spectrum of commonly available arylboronic acids and aryl bromides to provide biaryls in very good yields. The catalyst system works very well in the synthesis of sterically hindered biaryls.

Synthesis of Diaryl $\alpha$-Diketones via Palladium Catalyzed Double Carbonylative Homo Coupling of Aryl Iodides with Carbon Monoxide

  • Kim Jin Il;Kim Nam Jung;Ryu Cheol Mo
    • Bulletin of the Korean Chemical Society
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    • v.9 no.1
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    • pp.30-32
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    • 1988
  • Symmetrical diaryl ${\alpha}-diketones$ were synthesized in moderately good yields through the palladium catalyzed reaction of aryl iodides with carbon monoxide. The reaction was tolerant of a wide variety of fuctionalities($OCH_3,\;CH_3,\;NO_2,\;OH,\;COOH$) on the aryl iodide. On the other hand, the similar reaction of aryl bromides or chlorides with carbon monoxide did not proceed.

Palladium Catalyzed Carbonylative Vinylation of Aryl Halides with Olefins and Carbon Monoxide

  • Kim, Jin-Il;Ryu, Cheol-Mo
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.246-250
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    • 1987
  • The reaction of aryl iodides or bromides with olefins in the presence of 1 mol % of $PdCl_2(PPh_3)_2$ and 3 equiv. of $n-Bu_3N\; at\; 100^{\circ}C$ in carbon monoxide atmosphere gave the corresponding aryl vinyl ketones in good yields with small amount of vinylated 1-aryl olefins. But, when the reaction was proceeded under the 10 atm of carbon monoxide, aryl vinyl ${\alpha}$-diketones and aryl vinyl ketones were obtained in moderate to good yields. The reaction was tolerant of a wide variety of functional groups on either the aryl halides or olefin compounds. Reactivity of aryl halide decrease in the order; aryl iodide > aryl bromide ${\gg}$aryl chloride. In general, the reaction proceeded well and gave good yields of aryl vinyl ketones and aryl vinyl ${\alpha}$-diketones when reactants are substituted with electron withdrawing groups.

Solvent Effects on the Solvolysis of 2-Aryl-1,1-dimethylethyl Bromides

  • 황영호;김성홍;지종기;여수동
    • Bulletin of the Korean Chemical Society
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    • v.19 no.3
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    • pp.349-353
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    • 1998
  • Solvolysis rates of substituted 2-aryl-1,1-dimethylethyl bromides (1) were determined in a variety of solvents such as aqueous mixtures of ethanol, acetone, 2,2,2-trifluoroethanol, and also mixtures of ethanol and TFE at 25 ℃, 35 ℃, and 45 ℃. The solvent effects were analyzed in terms of Winstein-Grunwald equation. The solvent effects of 1-4-MeO failed to give a single linear correlation against either Y or YCl (YBr), but exhibited a wide split pattern which could not be related to the solvent nucleophilicity. On the other hand 1-4-CH3 and 1-H gave a fairly good linearity. In the case of 1-4-MeO, a fairly good linearity was observed against YΔ defined from the solvolysis of 4-methoxyneophyl tosylate. It is assumed that resonance interaction between reaction site and aryl-π-system operates to give charge delocalization regardless of the different solvolysis mechanisms. The Hammett-Brown treatment of the solvolytic rate constant of compounds 1 was obtained non-linear two separated lines of - 1.06 to - 1.46, suggesting of mechanistic changeover from kc-ks to kΔ on going from electron-withdrawing to electron-donating substituents as a basis of 4-CH3 group.

Synthesis, Anthelmintic and Anti-inflammatory Activities of Some Novel Imidazothiazole Sulfides and Sulfones

  • Shetty, Nitinkumar S.;Khazi, Imtiyaz Ahmed M.;Ahn, Chul-Jin
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2337-2340
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    • 2010
  • A series of new 6-aryl-3-(3,4-dimethoxy-phenyl)-2-phenylsulfanyl-imidazo[2,1-b]-thiazole (5a-c) and 6-aryl-2-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)imidazo[2,1-b]- thiazole (6a-c) have been prepared and characterized by analytical and spectral methods. The title compounds 5a-c and 6a-c were obtained by the reaction of 4-(3,4-dimethoxy-phenyl)-5-phenylsulfanyl-thiazol-2-ylamine (3) and 5-benzenesulfonyl-4-(3,4-dimethoxy -phenyl)thiazol-2-ylamine (4) with various phenacyl bromides in anhydrous ethanol. These newly synthesized compounds (5a-c and 6a-c) were screened for their anthelmintic and anti-inflammatory activities, where they have displayed better activities.