Palladium-Catalyzed C–H Benzannulation of Functionalized Furans and Pyrroles with Alkynes

Palladium-Catalyzed C–H Benzannulation of Functionalized Furans and Pyrroles with Alkynes

Abstract 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...

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Veröffentlicht in:Synthesis (Stuttgart) 2021-09, Vol.53 (17), p.3001-3010
Hauptverfasser: Seo, Jia, Chen, Che-Wei, Lee, Woohyeong, Jeon, Ju Eun, Chen, Pei-Ling, Chuang, Shih-Ching, Joo, Jung Min
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container_end_page 3010
container_issue 17
container_start_page 3001
container_title Synthesis (Stuttgart)
container_volume 53
creator Seo, Jia
Chen, Che-Wei
Lee, Woohyeong
Jeon, Ju Eun
Chen, Pei-Ling
Chuang, Shih-Ching
Joo, Jung Min
description Abstract 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.
doi_str_mv 10.1055/a-1502-3641
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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. 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title Palladium-Catalyzed C–H Benzannulation of Functionalized Furans and Pyrroles with Alkynes
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