- Palladium-Catalyzed C-H Benzannulation of Functionalized Furans and Pyrroles with Alkynes
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A benzannulation strategy involving activation of two C-H bonds of five-membered heteroarenes was developed. Readily available furans and pyrroles stabilized by synthetically useful electron-withdrawing groups underwent Pd-catalyzed 1:2 annulation reactions with diaryl alkynes. A variety of functional groups, including ester, amide, ketone, aldehyde, and nitrile, on the heterocyclic cores were tolerated in the Pd-catalyzed oxidative reactions. In these reactions, the combination of 2,2-dimethylbutyric acid and its conjugate base facilitated metalation at the heteroaromatic rings and reoxidation of the Pd(0) species using oxygen as the terminal oxidant. This strategy provides fluorescent benzofuran and indole derivatives and is expected to allow for further development of functionalized polycyclic heteroaromatic compounds.
- Seo, Jia,Chen, Che-Wei,Lee, Woohyeong,Jeon, Ju Eun,Chen, Pei-Ling,Chuang, Shih-Ching,Joo, Jung Min
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p. 3001 - 3010
(2021/06/15)
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- Palladium-catalyzed three-component domino reaction for the preparation of benzo[b]thiophene and related compounds
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A simple and efficient palladium-catalyzed three-component domino reaction of bromothiophenes with internal alkynes has been developed to produce benzo[b]thiophenes in moderate to good yields. The Royal Society of Chemistry 2011.
- Huang, Huanan,Li, Jing,Zhao, Weining,Mei, Yanbo,Duan, Zheng
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supporting information; experimental part
p. 5036 - 5038
(2011/08/10)
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- Synthesis of condensed heteroaromatic compounds by palladium-catalyzed oxidative coupling of heteroarene carboxylic acids with alkynes
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The palladium-catalyzed oxidative coupling of indole-3-carboxylic acids with alkynes effectively proceeds in a 1:2 manner accompanied by decarboxylation to produce the corresponding 1,2,3,4-tetrasubstituted carbazoles, some of which exhibit solid-state fl
- Yamashita, Mana,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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supporting information; experimental part
p. 2337 - 2340
(2009/09/30)
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- Fused ring construction around pyrrole, indole, and related compounds via palladium-catalyzed oxidative coupling with alkynes
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(Chemical Equation Presented) The selective synthesis of 1,2,3,4-tetrasubstituted carbazoles can be performed effectively through the palladium-catalyzed oxidative coupling reactions of N-substituted indoles or their carboxylic acid derivatives with alkyn
- Yamashita, Mana,Horiguchi, Hakaru,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
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scheme or table
p. 7481 - 7488
(2010/01/06)
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