Precise Construction of SCF2H or SeCF2H Groups on Heteroarenes Generated in Situ from CF3-Containing 1,3-Enynes
Shengnan Jin1, Zhijie Kuang1, Qiuling Song1,2,3
1Institute of Next Generation Matter Transformation , College of Chemical Engineering and College of Material Sciences Engineering at Huaqiao University , 668 Jimei Boulevard , Xiamen , Fujian , China 361021.
Abstract:
A divergent strategy for precise construction of SCF2H or SeCF2H groups on heteroarenes generated in situ from CF3-containing 1,3-enynes was developed. Reactions of readily available 1,3-enynes with S8 and ClCF2H provided 3-SCF2H-4-CF3-thiophenes via a cascade thiophene construction/selective C3 position thiolation/difluoromethylthiolation process, as did a series of 3-SeCF2H-4-CF3-selenophenes by similar strategies. The plausible radical annulation process for the construction of the thiophene ring and difluorocarbene generated in situ was confirmed by experiment.
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