1464149-47-0Relevant academic research and scientific papers
Synthesis of allylic and propargylic trifluoromethyl thioethers by copper(i)-catalyzed trifluoromethylthiolation of allylic bromides and propargylic chlorides
Rong, Mingguang,Li, Dongzhe,Huang, Ronglu,Huang, Yangjie,Han, Xiaoyan,Weng, Zhiqiang
, p. 5010 - 5016 (2014/08/18)
An efficient method is reported for the copper(I)-catalyzed trifluoromethylthiolation of allylic bromides by using elemental sulfur and CF3SiMe3. This rate of this transformation was significantly accelerated in the presence of 18-crown-6, and the reaction afforded the desired products in moderate to excellent yields with high stereo- and regioselectivity. This method can tolerate a number of functional groups and provides facile access to a variety of allylic trifluoromethyl thioethers. The copper(I)-catalyzed trifluoromethylthiolation of propargylic chlorides was also investigated. A plausible mechanism that involves an allylcopper(III) intermediate is proposed.
Copper(I) trifluoromethylthiolate complex bearing triphenylphosphine ligand for nucleophilic trifluoromethylthiolation of allylic bromides
Wang, Zhiyuan,Tu, Qiqi,Weng, Zhiqiang
supporting information, p. 830 - 834 (2014/03/21)
Copper(I) trifluoromethylthiolate complex (PPh3) 2Cu(SCF3) (1) has been synthesized from a convenient reaction of CuF2 with CF3SiMe3 and S 8 in the presence of triphenylphosphine. The crystal structure of complex 1 has been determined by X-ray crystallography. In the solid state, complex 1 exists as a monomeric copper(I) species with a three-coordinated trigonal planar geometry. Complex 1 reacted with a wide range of allylic bromides to afford corresponding allylic trifluoromethyl thioethers in moderate to good yields. Several functional groups, including alkyl, alkoxy, nitro, halides and geranyl groups, are tolerated.
Ruthenium-catalyzed regioselective allylic trifluoromethylthiolation reaction
Ye, Ke-Yin,Zhang, Xiao,Dai, Li-Xin,You, Shu-Li
, p. 12106 - 12110 (2015/01/09)
An efficient Ru-catalyzed regioselective allylic trifluoromethylthiolation reaction of allylic carbonates was developed. The linear allylic trifluoromethyl thioethers were obtained in 52-91% yields. Mechanistic investigation revealed that this reaction proceeds via a double allylic trifluoromethylthiolation sequence.
Nucleophilic trifluoromethylthiolation of allylic bromides: A facile preparation of allylic trifluoromethyl thioethers
Tan, Jianwei,Zhang, Guoting,Ou, Yangli,Yuan, Yaofeng,Weng, Zhiqiang
, p. 921 - 926 (2013/08/23)
A facile preparation of allylic trifluoromethyl thioethers was achieved by using a copper reagent. The reaction of (bpy)Cu(SCF3) with various allylic bromides afforded the desired trifluoromethylthiolation products in good to excellent yields with high stereo- and regioselectivity. Common functional groups such as alkyl, alkoxy, trifluoromethyl, nitro, halides and geranyl are well tolerated. A facile preparation of allylic trifluoromethyl thioethers was achieved by the reaction of (bpy)Cu(SCF3) with allylic bromides. This protocol afforded the desired trifluoromethylthiolation products in good to excellent yields with high stereo- and regioselectivity. Important functional groups such as alkyl, alkoxy, trifluoromethyl, nitro, halides and geranyl are well tolerated. Copyright
