Ru(II)-Catalyzed Redox-Neutral C–H Olefination and Tandem Cyclization with Vinyl Sulfones: Leveraging Sulfinate Anion as a Leaving Group for the Synthesis of 3-Methyleneisoindolin-1-ones

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-02 DOI:10.1021/acs.orglett.4c03904

Tamanna Rana, Amit B. Pawar

引用次数: 0

Abstract

We developed a Ru(II)-catalyzed redox-neutral C–H olefination of N-methoxybenzamides with vinyl sulfones. The reaction is operationally simple and conducted at ambient temperature and does not require silver additives or external oxidants, making it suitable for late-stage functionalization. Notably, we leveraged the leaving group ability of sulfinate anion to synthesize 3-methyleneisoindolin-1-ones through a tandem C–H olefination/cyclization/elimination sequence at ambient temperature. Moreover, we successfully demonstrated the synthetic versatility of 3-methyleneisoindolin-1-one for the construction of an isoindolobenzazepine core.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.