Cu(II)-Catalyzed Synthesis of 4‑(1,4,5,6-Tetrahydropyridin-3-yl)-1,4-dihydroisoquinolin-3-ones from 4‑Diazoisoquinolin-3-ones

Cu(II)-Catalyzed Synthesis of 4‑(1,4,5,6-Tetrahydropyridin-3-yl)-1,4-dihydroisoquinolin-3-ones from 4‑Diazoisoquinolin-3-ones

We report a simple, efficient, and highly selective C–H bond insertion of copper carbenes generated in situ from 4-diazo-1,4-dihydroisoquinolin-3-ones into β-C­(sp2)–H bonds of N-sulfonyl enamides, which gave a series of 4-(1,4,5,6-tetrahydropyridin-3-yl)-1,4-dihydroisoquinolin-3­(2H)-ones in good t...

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Veröffentlicht in:Journal of organic chemistry 2022-03, Vol.87 (6), p.4088-4096
Hauptverfasser: Qi, Minghui, Suleman, Muhammad, Xie, Jianwei, Lu, Ping, Wang, Yanguang
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container_issue 6
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container_title Journal of organic chemistry
container_volume 87
creator Qi, Minghui
Suleman, Muhammad
Xie, Jianwei
Lu, Ping
Wang, Yanguang
description We report a simple, efficient, and highly selective C–H bond insertion of copper carbenes generated in situ from 4-diazo-1,4-dihydroisoquinolin-3-ones into β-C­(sp2)–H bonds of N-sulfonyl enamides, which gave a series of 4-(1,4,5,6-tetrahydropyridin-3-yl)-1,4-dihydroisoquinolin-3­(2H)-ones in good to excellent yields. Operationally simple and mild reaction conditions, a cheap catalyst, readily accessible starting materials, and a broad substrate scope are the merits of this reaction.
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title Cu(II)-Catalyzed Synthesis of 4‑(1,4,5,6-Tetrahydropyridin-3-yl)-1,4-dihydroisoquinolin-3-ones from 4‑Diazoisoquinolin-3-ones
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