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  • Hydrobromic Acid catalyzed friedel crafts type reactions of naphthols
    RSC Advances, 2014
    Co-Authors: Hongjuan Yuan, Mang Wang, Yingjie Liu, Qun Liu
    Abstract:

    Catalyzed by 10 mol% of Hydrobromic Acid, hydroxyalkylation and allylation-iodocyclization of naphthols proceeded smoothly under mild conditions. In contrast, other Bronsted Acids tested, including HCl, HI, HBF4, HPF6, TFA, PTSA, H2SO4, TfOH etc., are almost ineffective under identical conditions or require harsh reaction conditions.

  • Hydrobromic Acid-catalyzed Friedel–Crafts type reactions of naphthols
    RSC Adv., 2014
    Co-Authors: Hongjuan Yuan, Mang Wang, Yingjie Liu, Qun Liu
    Abstract:

    Catalyzed by 10 mol% of Hydrobromic Acid, hydroxyalkylation and allylation-iodocyclization of naphthols proceeded smoothly under mild conditions. In contrast, other Bronsted Acids tested, including HCl, HI, HBF4, HPF6, TFA, PTSA, H2SO4, TfOH etc., are almost ineffective under identical conditions or require harsh reaction conditions.

  • Unexpected Hydrobromic Acid‐Catalyzed C ? C Bond‐Forming Reactions and Facile Synthesis of Coumarins and Benzofurans Based on Ketene Dithioacetals
    Chemistry (Weinheim an der Bergstrasse Germany), 2010
    Co-Authors: Hongjuan Yuan, Mang Wang, Jun Liu, Yingjie Liu, Lili Wang, Qun Liu
    Abstract:

    Hydrobromic Acid was found to be a unique catalyst in CC bond-forming reactions with ketene dithioacetals. Distinctly different from other Acids (including Lewis and Bronsted Acids), the remarkable catalytic performance of Hydrobromic Acid in catalytic amounts was observed in the “Acid”-catalyzed reactions of readily available functionalized ketene dithioacetals 1 with various electrophiles. Under the catalysis of 0.1 equivalents of Hydrobromic Acid, the reaction of 1 with carbonyl compounds 2 a–l gave polyfunctionalized penta-1,4-dienes 3 or conjugated dienes 4 in good to excellent yields. The reaction tolerated a broad range of substituents on both the ketene dithioacetals 1 and the carbonyl compounds 2. Application of this efficient CC bond-forming method generated coumarins 5 and benzofurans 7 under mild, metal-free conditions by Hydrobromic Acid-catalyzed reactions of 1 with salicylaldehydes 2 m–o and p-quinones 6 a–d, respectively. A new reactive species, a sulfur-stabilized carbonium ylide, formed depending on the nature of the counterion, and this was proposed as the key intermediate in the unique catalysis of Hydrobromic Acid.

  • Unexpected Hydrobromic Acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene dithioacetals
    Chemistry - A European Journal, 2010
    Co-Authors: Hongjuan Yuan, Yi-qun Liu, Likui Wang, Mang Wang, Jun Liu, Qun Liu
    Abstract:

    Hydrobromic Acid was found to be a unique catalyst in C-C bond-forming reactions with ketene dithioacetals. Distinctly different from other Acids (including Lewis and Brønsted Acids), the remarkable catalytic performance of Hydrobromic Acid in catalytic amounts was observed in the "Acid"-catalyzed reactions of readily available functionalized ketene dithioacetals 1 with various electrophiles. Under the catalysis of 0.1 equivalents of Hydrobromic Acid, the reaction of 1 with carbonyl compounds 2a-l gave polyfunctionalized penta-1,4-dienes 3 or conjugated dienes 4 in good to excellent yields. The reaction tolerated a broad range of substituents on both the ketene dithioacetals 1 and the carbonyl compounds 2. Application of this efficient C-C bond-forming method generated coumarins 5 and benzofurans 7 under mild, metal-free conditions by Hydrobromic Acid-catalyzed reactions of 1 with salicylaldehydes 2m-o and p-quinones 6a-d, respectively. A new reactive species, a sulfur-stabilized carbonium ylide, formed depending on the nature of the counterion, and this was proposed as the key intermediate in the unique catalysis of Hydrobromic Acid.

Daniel A. Dickman - One of the best experts on this subject based on the ideXlab platform.

Hongjuan Yuan - One of the best experts on this subject based on the ideXlab platform.

  • Hydrobromic Acid catalyzed friedel crafts type reactions of naphthols
    RSC Advances, 2014
    Co-Authors: Hongjuan Yuan, Mang Wang, Yingjie Liu, Qun Liu
    Abstract:

    Catalyzed by 10 mol% of Hydrobromic Acid, hydroxyalkylation and allylation-iodocyclization of naphthols proceeded smoothly under mild conditions. In contrast, other Bronsted Acids tested, including HCl, HI, HBF4, HPF6, TFA, PTSA, H2SO4, TfOH etc., are almost ineffective under identical conditions or require harsh reaction conditions.

  • Hydrobromic Acid-catalyzed Friedel–Crafts type reactions of naphthols
    RSC Adv., 2014
    Co-Authors: Hongjuan Yuan, Mang Wang, Yingjie Liu, Qun Liu
    Abstract:

    Catalyzed by 10 mol% of Hydrobromic Acid, hydroxyalkylation and allylation-iodocyclization of naphthols proceeded smoothly under mild conditions. In contrast, other Bronsted Acids tested, including HCl, HI, HBF4, HPF6, TFA, PTSA, H2SO4, TfOH etc., are almost ineffective under identical conditions or require harsh reaction conditions.

  • Unexpected Hydrobromic Acid‐Catalyzed C ? C Bond‐Forming Reactions and Facile Synthesis of Coumarins and Benzofurans Based on Ketene Dithioacetals
    Chemistry (Weinheim an der Bergstrasse Germany), 2010
    Co-Authors: Hongjuan Yuan, Mang Wang, Jun Liu, Yingjie Liu, Lili Wang, Qun Liu
    Abstract:

    Hydrobromic Acid was found to be a unique catalyst in CC bond-forming reactions with ketene dithioacetals. Distinctly different from other Acids (including Lewis and Bronsted Acids), the remarkable catalytic performance of Hydrobromic Acid in catalytic amounts was observed in the “Acid”-catalyzed reactions of readily available functionalized ketene dithioacetals 1 with various electrophiles. Under the catalysis of 0.1 equivalents of Hydrobromic Acid, the reaction of 1 with carbonyl compounds 2 a–l gave polyfunctionalized penta-1,4-dienes 3 or conjugated dienes 4 in good to excellent yields. The reaction tolerated a broad range of substituents on both the ketene dithioacetals 1 and the carbonyl compounds 2. Application of this efficient CC bond-forming method generated coumarins 5 and benzofurans 7 under mild, metal-free conditions by Hydrobromic Acid-catalyzed reactions of 1 with salicylaldehydes 2 m–o and p-quinones 6 a–d, respectively. A new reactive species, a sulfur-stabilized carbonium ylide, formed depending on the nature of the counterion, and this was proposed as the key intermediate in the unique catalysis of Hydrobromic Acid.

  • Unexpected Hydrobromic Acid-catalyzed C-C bond-forming reactions and facile synthesis of coumarins and benzofurans based on ketene dithioacetals
    Chemistry - A European Journal, 2010
    Co-Authors: Hongjuan Yuan, Yi-qun Liu, Likui Wang, Mang Wang, Jun Liu, Qun Liu
    Abstract:

    Hydrobromic Acid was found to be a unique catalyst in C-C bond-forming reactions with ketene dithioacetals. Distinctly different from other Acids (including Lewis and Brønsted Acids), the remarkable catalytic performance of Hydrobromic Acid in catalytic amounts was observed in the "Acid"-catalyzed reactions of readily available functionalized ketene dithioacetals 1 with various electrophiles. Under the catalysis of 0.1 equivalents of Hydrobromic Acid, the reaction of 1 with carbonyl compounds 2a-l gave polyfunctionalized penta-1,4-dienes 3 or conjugated dienes 4 in good to excellent yields. The reaction tolerated a broad range of substituents on both the ketene dithioacetals 1 and the carbonyl compounds 2. Application of this efficient C-C bond-forming method generated coumarins 5 and benzofurans 7 under mild, metal-free conditions by Hydrobromic Acid-catalyzed reactions of 1 with salicylaldehydes 2m-o and p-quinones 6a-d, respectively. A new reactive species, a sulfur-stabilized carbonium ylide, formed depending on the nature of the counterion, and this was proposed as the key intermediate in the unique catalysis of Hydrobromic Acid.

Michael E Elisseou - One of the best experts on this subject based on the ideXlab platform.

E. Michael Elisseou - One of the best experts on this subject based on the ideXlab platform.