从子爵二溴烯烃和子爵二溴烯烃化学选择性制备炔烃

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-09 DOI:10.1021/acs.orglett.4c03483

Hyuga Okumura, Nurcahyo Iman Prakoso, Tatsuya Morozumi, Taiki Umezawa

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引用次数: 0

摘要

介绍了用 iPrMgCl-LiCl（Turbo Grignard 试剂）将沧基和宝石基二溴烯烃还原转化为相应的炔烃的过程。该反应在各种官能团（如醚、酯或氨基甲酸酯）存在的温和条件下进行，产率高。由于反应的选择性，容易制备的沧二溴烯烃被认为是炔烃对亲电体的保护基团。尽管丁基锂已被广泛用于在科里-富克斯炔合成法中将沧二溴烯烃转化为炔烃，但我们在此报告了用于炔烃合成的其他温和且具有化学选择性的反应条件。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Chemoselective Preparation of Alkynes from Vicinal and Geminal Dibromoalkenes

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Chemoselective Preparation of Alkynes from Vicinal and Geminal Dibromoalkenes

The reductive conversion of vicinal and geminal dibromoalkenes into the corresponding alkynes with iPrMgCl-LiCl (Turbo Grignard reagent) is described. This reaction proceeded in the presence of various functional groups such as ethers, esters, or carbamates under mild conditions in high yields. Due to the selective reactivity, the easily prepared vic-dibromoalkene is considered to be a protecting group of alkyne toward an electrophile. Although butyl lithium has been widely used for the conversion of gem-dibromoalkenes into alkynes in the Corey–Fuchs alkyne synthesis, we report here alternative mild and chemoselective reaction conditions for alkyne synthesis.

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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.