Copper-catalyzed thiocyanation of cyclobutanone oxime esters using ammonium thiocyanate

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-...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-02, Vol.22 (7), p.1466-1474
Main Authors: Zhao, Xia, Sun, Tengteng, Gu, Wenxin, Qin, Jingwen, Lu, Kui, Ye, Fei
Format: Article
Language:English
Subjects:
Alkanes
Ammonium
Catalysts
Copper
Esters
Oxime esters
Phosphorothioate
Substitutes
Sulfur
Thiocyanates
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Summary: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. A copper-catalyzed thiocyanation of cyclobutanone oxime esters by potassium ammonium thiocyanate was achieved for the first time. Subsequent derivatization of thiocyano substituted alkylnitriles led to various sulfur-containing alkylnitriles.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01898a