Solvent Controlled Chemodivergent Sulfonyl Addition into Enynones: Synthesis of α-Furyl Sulfones and Stereodefined Vinyl Sulfones

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2024-12-28 DOI:10.1021/acs.joc.4c02165
Antony Haritha Mercy A, Padma Priya V. R, Natarajan K, Ramesh Kataria, Ganesh Chandra Nandi
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Abstract

Sodium salt of aryl sulfinic acid reacts with enynone in a different manner, yielding α-furyl sulfone and stereodefined vinyl sulfone in toluene and EtOH respectively in the presence of ZnCl2. The salient features of this protocol include chemoselectivity, broad substrate scope, high efficiency, high yield, and easy purification. The synthetic utilities of the products are demonstrated by cycloaddition and cis–trans photoisomerization reactions.

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溶剂控制化学发散磺酰加成成烯酮:α-呋喃基砜和立体乙烯基砜的合成
芳基亚磺酸钠盐在ZnCl2的存在下,以不同的方式与炔发生反应,分别在甲苯和乙醚中生成α-呋喃砜和立体乙烯基砜。该方法具有化学选择性强、底物范围广、效率高、收率高、易纯化等特点。通过环加成反应和顺反光异构反应证明了产物的合成用途。
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来源期刊
Journal of Organic Chemistry
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.
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