69127-72-6Relevant articles and documents
A mild and fast photocatalytic trifluoromethylation of thiols in batch and continuous-flow
Straathof, Natan J. W.,Tegelbeckers, Bart J. P.,Hessel, Volker,Wang, Xiao,Nol, Timothy
, p. 4768 - 4773 (2015/01/09)
S-CF3 bonds are important structural motifs in various pharmaceutical and agrochemical compounds. However, their preparation remains a major challenge in synthetic organic chemistry. Here, we report the development of a mild and fast photocatalytic trifluoromethylation of thiols. The combination of commercially available Ru(bpy)3Cl2, visible light and inexpensive CF3I gas proved to be an efficient method for the direct trifluoromethylation of thiols. The protocol is demonstrated on a wide range of aromatic, hetero-aromatic and aliphatic substrates in both batch and continuous microflow (32 examples, 52-98% yield). Process intensification through continuous microflow application resulted in a 15-fold increase in production rate (0.25 mmol min-1) due to improved gas-liquid mass transfer, enhanced irradiation as well as convenient handling of the gaseous CF3 source. Furthermore, the efficiency of the flow process allowed to reduce the amount of CF3I (1.1 equivalent) to reach full conversion. This journal is
Reactions of Bromotrifluoromethane and Related Halides. Part 12. Transformation of Disulfides into Perfluoroalkyl Sulfides in the Presence of Sulfoxylate Anion Radical Precursors
Clavel, Jean-Louis,Langlois, Bernard,Nantermet, Roland,Tordeux, Marc,Wakselman, Claude
, p. 3371 - 3376 (2007/10/02)
Perfluoroalkyl sulfides are prepared by reaction of perfluoroalkyl halides with disulfides in the presence of sulfoxylate anion radical precursors.Aliphatic, aromatic and heteroaromatic disulfides bearing cyano, ester and amino functional groups have been employed; a variety of perhalogenoalkanes can also be employed, e.g.CF3(CF2)nI, CF3Br, CF2Br2, CF2BrCl, CFCl3 and CF2ClCFCl2.The most convenient sulfoxylate anion radical precursor for this reaction is formed by a combination of sodium formate and sulfur dioxide.
PERFLUOROALKYLATION OF THIOLS. EVIDENCE FOR A RADICAL CHAIN PROCESS
Feiring, Andrew E.
, p. 191 - 204 (2007/10/02)
Perfluoroalkyl sulfides are formed from primary or secondary perfluoroalkyl iodides and aromatic or alphatic thiolates without UV irradiation.Perfluoroalkyl radicals are intermediates as demonstrated by inhibition and trapping studies.