Rh(III)-Catalyzed [3 + 4] Annulation of 3-Arylisoindolinones with 2-Methylidenetrimethylene Carbonate via C–H Activation to Access Isoindolinone Spirobenzoxepines

A Rh(III)-catalyzed C-H activation/annulation of 3-aryl-3-hydroxyisoindolinones with 2-methylidenetrimethylene carbonate has been developed. This method leads to the synthesis of seven-membered isoindolinone spirobenzoxepines through sequential C-C and C-O bond formations, which are interesting scaffolds in drug discovery. Its synthetic application has also been demonstrated to highlight the versatility. In addition, this is the first example in which 2-methylidenetrimethylene carbonate serves as a C3O1 synthon to accomplish [3 + 4] annulation in transition-metal-catalyzed C-H activation reactions.

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Publication Details

Journal
Organic Letters
Published
2025-06-13
DOI
https://doi.org/10.1021/acs.orglett.5c01573
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Rh(III)-Catalyzed [3 + 4] Annulation of 3-Arylisoindolinones with 2-Methylidenetrimethylene Carbonate via C–H Activation to Access Isoindolinone Spirobenzoxepines

Li‐Ming Zhao, Ru-Jie Zhang, Hai-Shan Jin, Yan Wang
1 links
Organic Letters
Catalytic C–H Functionalization Methods
article

Rh(III)-Catalyzed [3 + 4] Annulation of 3-Arylisoindolinones with 2-Methylidenetrimethylene Carbonate via C–H Activation to Access Isoindolinone Spirobenzoxepines

Li‐Ming Zhao, Ru-Jie Zhang, Hai-Shan Jin, Yan Wang
article en

Abstract

A Rh(III)-catalyzed C-H activation/annulation of 3-aryl-3-hydroxyisoindolinones with 2-methylidenetrimethylene carbonate has been developed. This method leads to the synthesis of seven-membered isoindolinone spirobenzoxepines through sequential C-C and C-O bond formations, which are interesting scaffolds in drug discovery. Its synthetic application has also been demonstrated to highlight the versatility. In addition, this is the first example in which 2-methylidenetrimethylene carbonate serves as a C3O1 synthon to accomplish [3 + 4] annulation in transition-metal-catalyzed C-H activation reactions.

Organic LettersVol. 27(25)
Jiangsu Normal University (CN)
Science and Technology Support Program of Jiangsu Province
Openalex Percentile: Top 90%
Catalytic C–H Functionalization Methods
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