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Cobalt-Catalyzed Switchable [4 + 1] and [4 + 1 + 1] Spirocyclization of Aromatic Amides with 2-Diazo-1H-indene-1,3(2H)-dione: Access to Spiro Indene-2,1’-isoindolinones and Spiro Isochro-man-3,1’-isoindolinones
  • +3
  • Bin Li,
  • Mengmeng Xie,
  • Jingyu Li,
  • Nana Shen,
  • Xinying Zhang,
  • Xuesen Fan
Bin Li
Henan Normal University

Corresponding Author:libin@htu.edu.cn

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Mengmeng Xie
Henan Normal University
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Jingyu Li
Henan Normal University
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Nana Shen
Henan Normal University
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Xinying Zhang
Henan Normal University
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Xuesen Fan
Henan Normal University
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Abstract

Herein we report a condition-controlled divergent synthesis of spiro indene-2,1’-isoindolinones and spiro isochroman-3,1’-isoindolinones through cobalt-catalyzed formal [4 + 1] and [4 + 1 + 1] spirocyclization of aromatic amides with 2-diazo-1H-indene-1,3(2H)-dione. When the reaction is carried out under air in ethyl acetate, spiro indene-2,1’-isoindolinones are formed through Co(II)-catalyzed C−H/N−H [4 + 1] spirocyclization. When the reaction is run under O2 in CH3CN, on the other hand, spiro isochroman-3,1’-isoindolinones are generated through Baeyer-Villiger oxidation of the in situ formed spiro indene-2,1’-isoindolinones with O2 as a cheaper and environmental-friendly oxygen source. In general, these protocols have advantages such as using non-precious and earth-abundant metal catalyst, no extra additive, high efficiency and regioselectivity. A gram-scale synthesis and the removal of the directing group further highlight its utility.
21 Aug 2023Reviewer(s) Assigned
30 Aug 2023Review(s) Completed, Editorial Evaluation Pending
31 Aug 2023Editorial Decision: Revise Minor
25 Sep 20231st Revision Received
26 Sep 2023Assigned to Editor
26 Sep 2023Submission Checks Completed
26 Sep 2023Review(s) Completed, Editorial Evaluation Pending
26 Sep 2023Editorial Decision: Accept