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Pd-Catalyzed Cyanoselenylation of Internal Alkynes: Access to Tetrasubstituted Selenoenol Ethers.
Organic Letters ( IF 4.9 ) Pub Date : 2020-06-17 , DOI: 10.1021/acs.orglett.0c01582
Marcel Bürger , Sebastian H. Röttger , Maximilian N. Loch , Peter G. Jones , Daniel B. Werz

The intra- and intermolecular synthesis of selenium-substituted acyclic and heterocyclic acrylonitrile derivatives is presented. The 1,2-difunctionalization of several internal alkynes substituted not only by aliphatic and aromatic residues but also by heteroelements is realized by the Pd-catalyzed activation of aromatic and aliphatic selenocyanates. A high functional group tolerance allows straightforward access to a broad scope of tetrasubstituted olefins. X-ray studies of some products reveal noncovalent chalcogen–chalcogen interactions between oxygen and selenium.

中文翻译:

Pd催化的内部炔烃氰基硒化反应:获得四取代的硒烯醇醚。

提出了硒取代的无环和杂环丙烯腈衍生物的分子内和分子间合成。通过Pd催化的芳香族和脂肪族硒代氰酸酯的活化,不仅可以被脂肪族和芳香族残基取代,而且还可以被杂元素取代的多个内部炔烃的1,2-双官能化。较高的官能团耐受性允许直接获得广泛的四取代烯烃。对某些产品的X射线研究表明,氧和硒之间存在非共价硫属元素-硫属元素相互作用。
更新日期:2020-07-02
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