Copper(I)‐Mediated Direct Trifluoromethylthiolation of Allylic Halides with Elemental Sulfur and (Trifluoromethyl)trimethylsilane. Issue 16 (22nd April 2015)

• Record Type: Journal Article
• Authors: Li, Jue; Wang, Peiqiang; Xie, Fei‐Fei; Yang, Xi‐Gang; Song, Xiao‐Nan; Chen, Wei‐Dong; Ren, Jiangmeng; Zeng, Bu‐Bing
• Is Part Of: European journal of organic chemistry. Issue 16(2015)
• Page Start: 3568
• Page End: 3571
• Publication Date: 2015-04-22
• Subjects: Synthetic methods -- Allylic compounds -- Copper -- Fluorine -- Sulfur -- Reaction mechanisms; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500384
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new method has been developed for the copper‐mediated trifluoromethylthiolation of allylic halides by using potassium fluoride, elemental sulfur, and (trifluoromethyl)trimethylsilane in anhydrous N, N ‐dimethylformamide. This protocol provides facile access to a variety of allylic trifluoromethyl thioethers in moderate to good yields under mild, ligand‐free reaction conditions. Abstract : A novel, mild and efficient approach for the synthesis of allylic trifluoromethyl thioethers by using DMF as solvent, CuSCN as copper salt, dry KF as base, S8 and TMSCF3 as trifluoromethanethiol source at 45 °C was developed. The obvious advantages of this method are that the reaction proceeds smoothly under mild and ligand‐free conditions, with good yields, and with a wide range of substrates as well as inexpensive and non‐toxic reagents.