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使用硫氰酸铵对环丁酮肟酯进行铜催化的硫氰化反应。

Copper-catalyzed thiocyanation of cyclobutanone oxime esters using ammonium thiocyanate.

作者信息

Zhao Xia, Sun Tengteng, Gu Wenxin, Qin Jingwen, Lu Kui, Ye Fei

机构信息

College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key laboratory of Inorganic-organic Hybrid Functional Material Chemistry, Ministry of Education, Tianjin Normal University, Tianjin, 300387, China.

hina International Science and Technology Cooperation Base of Food Nutrition/Safety and Medicinal Chemistry, College of Biotechnology, Tianjin University of Science & Technology, C, Tianjin, 300457, China.

出版信息

Org Biomol Chem. 2024 Feb 14;22(7):1466-1474. doi: 10.1039/d3ob01898a.

DOI:10.1039/d3ob01898a
PMID:38284473
Abstract

A copper-catalyzed thiocyanation of cycloketone oxime esters with ammonium thiocyanate has been developed for the first time. This innovative approach allows access to cyano and thiocyano bifunctionally substituted alkanes, which can be further transformed into their respective trifluoromethylthiol-substituted or difluoromethylthiol-substituted alkylnitriles, alkynyl sulfides, and phosphorothioate esters. The readily available nature of ammonium thiocyanate and the cost-effectiveness of the copper catalyst make this method a promising strategy for the synthesis of sulfur-containing alkylnitriles.

摘要

首次开发了一种铜催化环酮肟酯与硫氰酸铵的硫氰化反应。这种创新方法能够合成氰基和硫氰基双官能团取代的烷烃,这些产物可进一步转化为各自的三氟甲硫基取代或二氟甲硫基取代的烷基腈、炔基硫醚和硫代磷酸酯。硫氰酸铵易于获得,且铜催化剂具有成本效益,这使得该方法成为合成含硫烷基腈的一种有前景的策略。

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