4.6 Article

Redox-neutral rhodium(iii)-catalyzed chemo- and regiospecific [4+1] annulation between benzamides and alkenes for the synthesis of functionalized isoindolinones

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 19, 期 45, 页码 9946-9952

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob01792f

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资金

  1. Zhejiang Provincial Natural Science Foundation of China [LQ19B020003, LY21B020003]
  2. Jinhua Science and Technology Bureau [2021-3-150]
  3. Jinhua Branch of Sichuan Industrial Institute of Antibiotics [1003, SIIAJH-202002, SIIAJH-202006]

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In this study, an electron-deficient alkene embedded with an oxidizing function/leaving group was used as a rare and nontraditional C-1 synthon to achieve a redox-neutral Rh(iii)-catalyzed chemo- and regioselective [4 + 1] annulation of benzamides for the synthesis of functionalized isoindolinones. This method demonstrated a broad substrate scope, good to excellent yields, excellent chemo- and regioselectivity, good tolerance of functional groups, and mild external-oxidant-free conditions.
Herein, using electron-deficient alkenes embedded with an oxidizing function/leaving group as a rare and nontraditional C-1 synthon, we have achieved the redox-neutral Rh(iii)-catalyzed chemo- and regioselective [4 + 1] annulation of benzamides for the synthesis of functionalized isoindolinones. This method features broad substrate scope, good to excellent yields, excellent chemo- and regioselectivity, good tolerance of functional groups and mild external-oxidant-free conditions.

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