分子内环化二氢芴-3-酮的一锅组装：一种功能化芴的方法。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-10-17 DOI:10.1021/acs.joc.5c01964

Chada Raji Reddy,Ankita Kumari,Adla Vijender,Shiva Kumar Kota Balaji,René Grée

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引用次数: 0

摘要

在此，我们揭示了一种由丙炔醇与炔基硅烯醇醚反应合成一种独特结构框架-二氢芴-3- 1的方法。在PPh3AuNTf2 （2mol %）的存在下，通过酸催化的硅烯醇醚丙基化反应生成烷基炔酮和随后的分子内环化（3+2环加成）。这种新型二氢芴-3- 1基序被发现是一种多功能前体，可提供多种功能化芴。

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One-Pot Assembly of Dihydrofluoren-3-ones via Intramolecular Annulation of Alkynyl-Alkynones: A Way to Functionalized Fluorenes.

Herein, we reveal an approach for the synthesis of a unique structural framework, dihydrofluoren-3-one, from the reaction of propargylic alcohol with alkynyl silyl enol ether. The transformation proceeds through acid-catalyzed propargylation of silyl enol ether leading to alkynyl-alkynones and subsequent intramolecular annulation (3+2 cycloaddition) in the presence of PPh3AuNTf2 (2 mol %). This novel dihydrofluoren-3-one motif was found to be a versatile precursor to provide diverse functionalized fluorenes.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.