Nickel-Catalyzed Enantioselective Carbo-Carbonylation of Alkenes Using Formic Acid as a CO Surrogate: Access to Oxindoles Bearing Chiral Quaternary Carbon

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-21 DOI:10.1021/acs.orglett.6c04269

Krishnamoorthy Kathirvel,Govindasamy Sekar

引用次数: 0

Abstract

Carbonylation reactions typically rely on toxic carbon monoxide gas, often under pressurized conditions. Herein, we report an enantioselective nickel-catalyzed carbonylative difunctionalization of activated olefins using formic acid as a safe and operationally simple CO surrogate under mild conditions. The reaction employs a chiral phosphine-based ferrocene ligand to furnish ester-functionalized oxindoles bearing stereogenic quaternary carbon centers in high yields and enantioselectivities. Isotopic-labeling and XPS studies support in situ CO generation and trapping by an alkyl-nickel intermediate.

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以甲酸为CO替代物的镍催化烯烃的对映选择性碳羰基化反应：获得含手性季碳的氧吲哚

羰基化反应通常依赖于有毒的一氧化碳气体，通常在加压条件下进行。在此，我们报道了在温和的条件下，用甲酸作为安全、操作简单的CO替代物，镍催化的活化烯烃羰基化双官能化反应。该反应采用手性膦基二茂铁配体，以高收率和对映选择性制备了具有立体碳中心的酯功能化氧吲哚。同位素标记和XPS研究支持烷基镍中间体原位生成和捕获CO。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.