Ready access to organoiodides: Practical hydroiodination and double-iodination of carbon-carbon unsaturated bonds with I2 |
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| Affiliation: | 1. Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China;2. National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Ibaraki 305-8565, Japan;3. Institute of Drug Discovery Technology, Ningbo University, Ningbo, Zhejiang 450052, China;1. Department of Chemistry, University of Louisville, Louisville, KY 40292, United States;2. Department of Chemistry and Physics, Bellarmine University, Louisville, KY 40205, United States;3. College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China;1. School of Physical Science and Technology, ShanghaiTech University, Shanghai, 201210, China;2. Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, China;3. Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China |
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| Abstract: | By using I2 or I2/H3PO3 system, various alkenes and alkynes were converted to the corresponding alkyl and alkenyl iodides in good yields. In the presence of I2, alkynes could be di-iodinated using H2O as the solvent in air at room temperature. This method also features the simple work-up procedure since the pure product could be obtained by extraction. Additionally, for the first time, combining with the non-toxic and cheap phosphonic acid H3PO3, alkenes and alkynes were also hydroiodinated successfully, which provides a simple and practical approach for synthesis of organoiodides. |
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| Keywords: | Organoiodides Hydroiodination Double-iodination Iodine phosphonic acid |
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