Palladium-catalyzed ring-opening/defluorinative coupling of gem-DFCPs with pyranones/pyridones

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-09-16 DOI:10.1016/j.tet.2024.134271
Ling-Juan Tang , Shun-Jun Ji , Zhong-Jian Cai
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Abstract

The monofluoroalkenes are found widespread applications in areas such as bioactive molecules, materials science and synthetic organic chemistry, therefore, investigating efficient methodologies to construct monofluoroalkenes is still in demand. In this paper, we reported an efficient synthesis of monofluoroalkenyl substituted pyranones/pyridones by using the gem-difluorocyclopropanes (gem-DFCPs) as monofluoroalkenyl precursors. In the presence of Palladium catalyst, the monofluoroalkenyl group was introduced into the C3 positions of pyranones/pyridones successfully. The reaction was featured with high regioselectivity, mild conditions, broad substrate scope, easy to scale up synthesis, which provided a novel avenue for the late-stagy modification of pyranones/pyridones.

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钯催化的 gem-DFCP 与吡喃酮/吡啶酮的开环/脱氟偶联
一氟烯烃在生物活性分子、材料科学和有机合成化学等领域有着广泛的应用,因此,研究构建一氟烯烃的高效方法仍然很有必要。在本文中,我们报道了一种以宝石-二氟环丙烷(gem-DFCPs)为单氟烯基前体,高效合成单氟烯基取代的吡喃酮/吡啶酮的方法。在钯催化剂存在下,成功地将单氟烯基引入吡喃酮/吡啶酮的 C3 位。该反应具有高区域选择性、条件温和、底物范围广、易于放大合成等特点,为吡喃酮/吡啶酮的晚期滞后修饰提供了一条新途径。
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来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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Contents continued Graphical abstract TOC Graphical abstract TOC Editorial Board Synthesis of dendritic self-immolative molecules triggered by reactive electrophilic alkylating agents: Assessment for colorimetric disclosure of such agents
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