Ruthenium-Catalyzed Intramolecular Allene–alkyne Cascade Cyclization: Access to the Sulfone-cyclopenta[a]naphthalene Core

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-01-29 DOI:10.1021/acs.orglett.4c04659
Puja Singh, Deepshikha, Nand Lal, Manoj V. Mane, Aslam C. Shaikh
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Abstract

A ruthenium-catalyzed intramolecular cascade cyclization of allene–alkyne has been achieved. This method offers a streamlined and atom-economical approach for the construction of sulfone bearing 1H-cyclopenta[a]naphthalenes, an important structural scaffold that exists in biologically active compounds. Our approach, backed by mechanistic insights from deuterium labeling, DFT calculations, and potential for reaction scale-up, presents synthetic chemists with an invaluable tool for efficiently producing a distinct carbon framework in a one-pot manner. This protocol is operationally simple, exhibiting a broad substrate scope with consistently high yields.

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钌催化的分子内烯-炔级联环化:进入砜基环戊并[a]萘核心
研究了钌催化的烯炔分子级联环化反应。该方法为构建含1h -环五[a]萘的砜提供了一种简化的原子经济方法,h -环五[a]萘是生物活性化合物中重要的结构支架。我们的方法,以氘标记,DFT计算和反应放大潜力的机理见解为基础,为合成化学家提供了一种宝贵的工具,可以有效地以一锅方式生产独特的碳框架。该协议操作简单,具有广泛的衬底范围和一贯的高产量。
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来源期刊
Organic Letters
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.
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