ID | 62194 |
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Author |
Asako, Sobi
Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
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Takahashi, Ikko
RIKEN Center for Sustainable Resource Science
Nakajima, Hirotaka
Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
Ilies, Laurean
RIKEN Center for Sustainable Resource Science
Takai, Kazuhiko
Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
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Abstract | With sodium being the most abundant alkali metal on Earth, organosodium compounds are an attractive choice for sustainable chemical synthesis. However, organosodium compounds are rarely used-and are overshadowed by organolithium compounds-because of a lack of convenient and efficient preparation methods. Here we report a halogen-sodium exchange method to prepare a large variety of (hetero)aryl- and alkenylsodium compounds including tri- and tetrasodioarenes, many of them previously inaccessible by other methods. The key discovery is the use of a primary and bulky alkylsodium lacking beta-hydrogens, which retards undesired reactions, such as Wurtz-Fittig coupling and beta-hydrogen elimination, and enables efficient halogen-sodium exchange. The alkylsodium is readily prepared in situ from neopentyl chloride and an easy-to-handle sodium dispersion. We believe that the efficiency, generality, and convenience of the present method will contribute to the widespread use of organosodium in organic synthesis, ultimately contributing to the development of sustainable organic synthesis by rivalling the currently dominant organolithium reagents. Halogen-sodium exchange reactions with neopentyl sodium provides access to a range of aryl and alkenyl organosodium compounds in situ, as an alternative to organolithium reagents.
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Published Date | 2021-05-24
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Publication Title |
Communications Chemistry
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Volume | volume4
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Issue | issue1
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Publisher | Nature Research
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Start Page | 76
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ISSN | 2399-3669
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Content Type |
Journal Article
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language |
English
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OAI-PMH Set |
岡山大学
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Copyright Holders | © The Author(s) 2021
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File Version | publisher
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Related Url | isVersionOf https://doi.org/10.1038/s42004-021-00513-2
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License | http://creativecommons.org/licenses/by/4.0/
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Funder Name |
Okayama University
RIKEN
KOBELCO ECO-Solutions CO., Ltd.
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