• Title/Summary/Keyword: Aryl iodides

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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.

A Direct Transformation of Aryl Aldehydes to Benzyl Iodides Via Reductive Iodination

  • Ruso, Jayaraman Sembian;Rajendiran, Nagappan;Kumaran, Rajendran Senthil
    • Journal of the Korean Chemical Society
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    • v.58 no.1
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    • pp.39-43
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    • 2014
  • A facile transformation of aryl aldehydes to benzyl iodides through one-pot reductive iodination is reported. This protocol displays remarkable functional group tolerance and the title compound was obtained in good to excellent yield.

Selective Copper-Catalyzed Azidation and Amination of Aryl Halides with Sodium Azide (구리 촉매에 의한 할로젠화 아릴과 아지도 소듐의 선택적 아지드화 및 아민화 반응)

  • Paik, Seunguk
    • Applied Chemistry for Engineering
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    • v.32 no.2
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    • pp.224-227
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    • 2021
  • A rapid and selective copper-catalyzed amination of aryl halides with sodium azide was established by using 10 mol % of CuI, and 20 mol % of N,N'-dimethylethylenediamine in DMSO under microwave irradiation for 10 min. The catalytic system with 4-substituted aryl iodides was found to be the most effective leading to a nearly complete conversion.

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.

Palladium-Catalyzed Cross-Coupling Reaction and Gold-Catalyzed Cyclization for Preparation of Ethyl 2-Aryl 2,3-Alkadienoates and α-Aryl γ-Butenolides

  • Mo, Jun-Tae;Hwang, Hoon;Lee, Phil-Ho
    • Bulletin of the Korean Chemical Society
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    • v.32 no.spc8
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    • pp.2911-2915
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    • 2011
  • Efficient synthetic method for the preparation of ethyl 2-aryl-2,3-alkadienoates through Pd-catalyzed selective allenyl cross-coupling reactions of aryl iodides with organoindiums generated in situ from indium and ethyl 4-bromo-2-alkynoate was developed. The cyclization reaction of ethyl 2-aryl-2,3-alkadienoates catalyzed by $AuCl_3$ and AgOTf in the presence of AcOH or TfOH produced various ${\alpha}$-aryl ${\gamma}$-butenolides or ${\gamma}$-substituted ${\alpha}$-aryl ${\gamma}$-butenolides.

A Study on N-Arylation of Indole Using Copper Nitrate or Copper Carbonate as a Catalyst (Copper Nitrate와 Copper Carbonate를 촉매로 이용한 Indole의 N-Arylation 연구)

  • Lee, Jun Young;Yang, Min Ho;Paik, Seung Uk
    • Applied Chemistry for Engineering
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    • v.19 no.6
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    • pp.629-632
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    • 2008
  • N-Arylation of indole with aryl iodides has been achieved by employing copper nitrate or copper cabonate as a catalyst, which might be more practical and economical over any other copper- or palladium-based catalysts for industrial applications. N,N'-dimethylethylenediamine was found to be the most effective with copper nitrate catalyst systems, while ethylenediamine was the most active with copper carbonate.

Synthesis of 1-(Benzotriazol-1-yl)alkyl Aryl Sulfones (1-(Benzotriazol-1-yl)alkyl Aryl Sulfone의 합성)

  • Hong, Young Seuk;Kim, Hyun Muk;Lee, Jeong Geun;Park, Yong Tae;Kim, Ho Sik
    • Journal of the Korean Chemical Society
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    • v.40 no.9
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    • pp.615-622
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    • 1996
  • (Benzotriazol-1-yl)arenesulfonylalkanes, 2a, 2b, 3a and 3b, were prepared by lithiation of 1-(benzotriazol-1-yl)arenesulfonylmethanes followed by reaction with alkyl iodides. Very bulky molecules such as 1,1-di(benzotriazol-1-yl)-1-aryl-1-thiophenoxymethanes 5, 1,1-di(benzotriazol-1-yl)-1-thiophenoxymethane 9a and 1,1-di(benzotriazol-1-yl)-1,1-dithiophenoxymethane 9b were synthesized. 1,1-Di(benzotriazol-1-yl)-1-benzenesulfoxymethane 10a and 1,1-di(benzotriazol-1-yl)-1-benzenesulfonylmethane 10b were also synthesized by the oxidation of compound 9a, while oxidation of sulfide group on compound 5 and 9b by m-CPBA were not successful. On the other hand, pyrolysis and hydrolysis of 3-(benzotriazol-1-yl)-3-toluenesulfonylpentane 3b gave 3-toluenesulfonyl-2-pentene 11 and diethyl ketone 13a, respectively, which means there are both C-N and C-S bond cleavages.

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