title: Triphenylphosphine-Mediated Deoxygenative Reduction of CF3 SO2 Na and Its Application for Trifluoromethylthiolation of Aryl Iodides.
abstract: We report herein a practical method for taming Langlois' reagent CF3 SO2 Na to generate CuSCF3 by a triphenylphospine-mediated deoxygenative reduction process. This chemistry highlights a novel utilization of the inherent CF3 S skeleton of Langlois' reagent as a CF3 S 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.
authors.affiliation: Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, 180 Xueyuan Street, Huixing Lu, Zigong, Sichuan, 643000, P.R. China. yangyiyoung@163.com.
authors.forename: Yi
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Department of Chemistry, Lehigh University, 6 E. Packer Ave., Bethlehem, PA, 18015, USA.
authors.forename: Long
authors.initials: L
authors.lastname: Xu
authors.affiliation: Department of Chemistry, Lehigh University, 6 E. Packer Ave., Bethlehem, PA, 18015, USA.
authors.forename: Siqi
authors.initials: S
authors.lastname: Yu
authors.affiliation: Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, 180 Xueyuan Street, Huixing Lu, Zigong, Sichuan, 643000, P.R. China.
authors.forename: Xiaoqiang
authors.initials: X
authors.lastname: Liu
authors.affiliation: Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, 180 Xueyuan Street, Huixing Lu, Zigong, Sichuan, 643000, P.R. China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, Lehigh University, 6 E. Packer Ave., Bethlehem, PA, 18015, USA. vicic@lehigh.edu.
authors.forename: David A
authors.identifier: http://orcid.org/0000-0002-4990-0355
authors.initials: DA
authors.lastname: Vicic
keywords: copper; cross-coupling; fluorine; organic chemistry; sulfur