Copper-Catalyzed Chemoselective Ring-Opening Hydroselenation and C-H Selenylation of Isoxazol-5-amines.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-16 DOI:10.1021/acs.orglett.5c02201

Yuan-Yi Lu,Junfen Han,Yu Teng,Meng-Qiang Cai,Hong-Shuang Li

引用次数: 0

Abstract

Copper-catalyzed highly chemoselective transformations of isoxazol-5-amines have been developed. The first ring-opening hydroselenation of isoxazol-5-amines with selenols or RSeSeR/H2O readily delivers 3-amino-2-selenoacrylamides in high yields, while the C-H selenylation of the substrates with diselenides at a low temperature produces 4-selenoisoxazoles with high efficiency. Both protocols demonstrate good functional group compatibility and mild reaction conditions under inexpensive copper catalysis. Mechanistic studies reveal that the presence of an amino group is indispensable for the successful implementation of the reactions.

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铜催化异恶唑-5胺的化学选择性开环氢硒化和C-H硒化。

研究了铜催化异恶唑-5-胺的高化学选择性转化。异恶唑-5-胺与硒醇或RSeSeR/H2O的第一次开环硒化反应容易高产地产生3-氨基-2-硒丙烯酰胺，而底物与二硒烯在低温下的C-H硒化反应则高效地产生4-硒代异恶唑。两种方案均表现出良好的官能团相容性和在廉价铜催化下温和的反应条件。机理研究表明，氨基的存在对于反应的成功实施是必不可少的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

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.