Synthesis of γ-Alkenylated δ-Sultones Via Brønsted Base-Catalyzed Annulative SuFEx Reaction of Allyl Ketones and Ethenesulfonyl Fluorides

IF 2.7 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-11-20 DOI:10.1002/ajoc.202400619
Qichao Zhang, Fang Zhang, Zhihang Wei, Xiangyi Shi, Lin He, Jichang Liu, Guangfen Du
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Abstract

A tandem annulation reaction of allyl ketones and β-aryl ethenesulfonyl fluorides has been described. Under the catalysis of Brønsted base, allyl ketones reacted with β-aryl ethenesulfonyl fluorides through a tandem intermolecular Michael addition-intramolecular SuFEx process to afford γ-alkenylated δ-sultones in good to excellent yields. In this reaction, no additional base was needed, and 4 Å molecular sieves were used as efficient HF scavenger to restrict the neutralization and deactivation of the Brønsted base catalyst.

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Brønsted碱催化烯丙基酮和乙烯磺酰氟环化SuFEx反应合成γ-烯基化δ-硫酮
描述了烯丙基酮与β-芳基乙烯磺酰氟的串联环化反应。在Brønsted碱的催化下,烯丙基酮与β-芳基乙烯磺酰氟化合物通过分子间Michael加成-分子内SuFEx反应得到了收率较高的γ-烯基化δ-磺酰氟化合物。在该反应中,不需要额外的碱,使用4个Å分子筛作为有效的HF清除剂来限制Brønsted碱催化剂的中和和失活。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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