Triphenylphosphine‐Mediated Deoxygenative Reduction of CF3SO2Na and Its Application for Trifluoromethylthiolation of Aryl Iodides |
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| Authors: | Prof Yi Yang Long Xu Siqi Yu Dr Xiaoqiang Liu Yu Zhang Prof David A Vicic |
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| Institution: | 1. Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Sichuan, P.R. China;2. Department of Chemistry, Lehigh University, Bethlehem, PA, USA |
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| Abstract: | We report herein a practical method for taming Langlois’ reagent CF3SO2Na to generate CuSCF3 by a triphenylphospine‐mediated deoxygenative reduction process. This chemistry highlights a novel utilization of the inherent CF3S skeleton of Langlois’ reagent as a CF3S feedstock under mild conditions. The CuSCF3 intermediate generated by this protocol can react with a wide array of supporting ligands to furnish several air‐stable LCu(SCF3)] complexes as valuable trifluoromethylthiolating agents. In addition, the CuSCF3 intermediate can be directly employed for the trifluoromethylthiolation of (hetero)aryl iodides with operational simplicity and atomic efficiency. |
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| Keywords: | copper cross-coupling fluorine organic chemistry sulfur |
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