The Perfluorophenylation Of Thiocyanates And 3-iodine-Indoles

The application value of fluorine-contained compounds as pharmaceuticals,agrochemicals and material is increasing.Therefore,the development of efficient ways of introducing fluorine atom and fluorine-containing group into organic compounds has become one of the hottest areas of organic synthesis these days.Nucleophilic fluorination is one of the most effective approaches to synthesize organic fluorides,which not only provides various fluorinated building blocks for further elaborations,but also is able to directly introduce fluorine atom(s)to pharmaceutical and agrochemical molecules.Based on the previous reported,we developed the synthesis methods of pentafluorophenyl sulfides and 3-(perfluorophenyl)-indole compounds with triethoxy(perfluorophenyl)silane and pentafluorobenzene as the source of perfluorophenyl group.1)A method for the synthesis of pentafluorophenyl sulfides from organic thiocyanates and triethoxy(perfluorophenyl)silane has been rported.To obtain the optimal reaction condition of this process,a series reaction condition were investigate.With the optimal conditions in hand,the scope of this reaction was explored.Various pentafluorophenyl sulfides derivatives could be easily prepared under mild condition without transition metal catalyst in good yields via this reaction.Combining with GC-MS analysis,NMR spectrum and a series of experiments,we proposed a feasible reaction mechanism of this reaction.2)A method of synthesis for 3-perfluorophenyl-indole from pentafluobenzene and 3-iodine-indole compound has been developed.Synthesis of 3-perfluorophenyl-indole via pentafluobenzene and 3-iodine-indole compounds was investigated.The reaction of 3-iodine-indole compounds and pentafluorobenzene was set as the model reaction to investigate the optimal condition of this process.Pd catalysts,phosphine ligand,additives,solvents,reaction temperatures and reaction time were optimized.With the optimal conditions in hand,the scope of this reaction was explored.3-Perfluorophenyl-indole compounds were synthesized in good yields.Based on the previous reported and a series of experiments,a plausible mechanism was proposed.