title: Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization.
abstract: An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.
authors.affiliation: †State Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.
authors.forename: Song
authors.initials: S
authors.lastname: Song
authors.affiliation: †State Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.
authors.forename: Xiang
authors.initials: X
authors.lastname: Sun
authors.affiliation: †State Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.
authors.forename: Xinwei
authors.initials: X
authors.lastname: Li
authors.affiliation: †State Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.
authors.forename: Yizhi
authors.initials: Y
authors.lastname: Yuan
authors.affiliation: †State Key Laboratory of Natural and Biomimetic Drugs, Peking University, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.|‡State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
authors.forename: Ning
authors.initials: N
authors.lastname: Jiao
mesh_terms: D000143:Acids / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D054879:Halogenation; D018054:Hydrobromic Acid / Q000737:chemistry*; D017613:Iodine Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000143:Acids; D001555:Benzene Derivatives; D001688:Biological Products; D017613:Iodine Compounds; D018054:Hydrobromic Acid; C010466:hydroiodic acid; D004121:Dimethyl Sulfoxide