- Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature
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The unsymmetrical biaryls (Ar1-Ar2) produced by the catalytic cross-couplings of aryl halides (Ar1-halo) with aryl metallics (Ar2-M) in the loading ratio of 1:1 are popular in chemical synthesis. In contrast, there has been less precedence on the same biaryls produced effectively from two normal aryl C-H bonds with equivalent loading. Here, we report that, in a palladium/oxidant/acid catalytic system at room temperature, one arene (Ar1-H, 1 equiv) can highly selectively couple with the other one (Ar2-H, 1 equiv) to afford the target Ar1-Ar2 just by controlling the directing groups and the substituted groups on their phenyl rings. The utility of this one-one cross-coupling is also demonstrated by synthesis of a few bioactive molecules.
- Mei, Chong,Zhao, Mengdi,Lu, Wenjun
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p. 2714 - 2733
(2021/02/01)
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- Ligand Promoted Olefination of Anilides for Indirectly Introducing Fluorinated Functional Groups via Palladium Catalyst
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We report a palladium-catalyzed, ligand promoted, C-H fluorine-containing olefination of anilides with 4-bromo-3,3,4,4-tetrafluorobutene as the fluorinated reagent, which has a potential transformation into other compounds due to its -CF2CF2Br functional group. -CF2CF2H was obtained by using the mild reducing agent sodium borohydride. Bioactive compounds such as aminoglutethimide derivative and propham were well-tolerated in this reaction, both of which highlight the synthetic importance of this method.
- Wang, Dongjie,Xu, Xu,Zhang, Jingyu,Zhao, Yingsheng
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p. 2696 - 2705
(2021/02/27)
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- Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature
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The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.
- Mei, Chong,Lu, Wenjun
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p. 4812 - 4823
(2018/04/26)
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- Amine Activation: Synthesis of N-(Hetero)arylamides from Isothioureas and Carboxylic Acids
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A novel method for N-(hetero)arylamide synthesis based on rarely explored amine activation, rather than classical acid activation, is reported. The activated amines are easily prepared using a three-component reaction with commercial reagents. The new method shows a broad scope including challenging amides not (efficiently) accessible via classical protocols.
- Zhu, Yan-Ping,Sergeyev, Sergey,Franck, Philippe,Orru, Romano V. A.,Maes, Bert U. W.
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supporting information
p. 4602 - 4605
(2016/09/28)
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- CuCl-catalyzed ortho trifluoromethylation of arenes and heteroarenes with a pivalamido directing group
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The CuCl catalyzed direct trifluoromethylation of sp2 C-H bonds has been realized, using the Togni reagent as the CF3 source. This reaction achieves the goal of regio-selectively converting C-H into C-CF 3 with ecological and readily available starting materials.
- Cai, Shangjun,Chen, Chao,Sun, Zelin,Xi, Chanjuan
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p. 4552 - 4554
(2013/06/04)
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- Improved Process for the Preparation of 2-Methyl-3-trifluoromethylaniline: A Versatile Intermediate for Flunixin Synthesis
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A detailed new experimental investigation into the synthesis of Flunixin via 2-methyl-3-trifluoromethylaniline is described.The coupling process between 2-methyl-3-trifluoromethylaniline and 2-chloronicotinate was achieved stoichiometrically and in high yield, when ethylene glycol was used as reaction solvent at 160 deg C.
- Jaouhari, Rabih,Quinn, Philip
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p. 2243 - 2246
(2007/10/02)
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- Preparation of substituted anilino-nicotinic acid derivatives
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Substituted anilino-nicotinic acid derivatives are readily prepared from the condensation of two intermediates, 2-alkyl-3-perfluoroalkyl-anilines and alkyl 2-chloronicotinates. The 2-alkyl-3-perfluoroalkyl-aniline intermediate can be prepared via a novel three step synthesis. 3-Perfluoroalkyl-anilines are reacted with an amine directing protecting group reagent to protect the amine. The protected amine is then alkylated, and finally, the directing group is removed to form the 2-alkyl-3-perfluoroalkyl-aniline intermediate. The 2-alkyl-3-perfluoroalkyl-aniline intermediate is condensed with the alkyl 2-chloronicotinate to form the anilino-nicotinic acid derivative.
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- Quinolyloxyacetamides
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Quinoline derivatives of formula: STR1 in which either R 1 denotes trifluoromethyl, R 2 and R 3 form, together with the nitrogen atom to which they are attached, morpholino and R 4 denotes a 4-methylphenyl, 4-chlorophenyl, 2-, 3- or 4-fluorophenyl, 4-meth
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