Sulfonium-aided coupling of aromatic rings via sigmatropic rearrangement
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- YORIMITSU Hideki
- Department of Chemistry, Graduate School of Science, Kyoto University
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- PERRY Gregory J. P.
- Department of Chemistry, Graduate School of Science, Kyoto University
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<p>Biaryl synthesis continues to occupy a central role in chemical synthesis. From blockbuster drug molecules to organic electronics, biaryls present numerous possibilities and new applications continue to emerge. Transition-metal-catalyzed coupling reactions represent the gold standard for biaryl synthesis and the mechanistic steps, such as reductive elimination, are well established. Developing routes that exploit alternative mechanistic scenarios could give unprecedented biaryl structures and expand the portfolio of biaryl applications. We have developed metal-free C–H/C–H couplings of aryl sulfoxides with phenols to afford 2-hydroxy-2′-sulfanylbiaryls. This cascade strategy consists of an interrupted Pummerer reaction and [3,3] sigmatropic rearrangement. Our method enables the synthesis of intriguing aromatic molecules, including oligoarenes, enantioenriched dihetero[8]helicenes, and polyfluorobiaryls. From our successes in aryl sulfoxide/phenol couplings and a deeper understanding of sigmatropic rearrangements for biaryl synthesis, we have established related methods, such as aryl sulfoxide/aniline and aryl iodane/phenol couplings. Overall, our fundamental interests in underexplored reaction mechanisms have led to various methods for accessing important biaryl architectures.</p>
収録刊行物
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- Proceedings of the Japan Academy. Ser. B: Physical and Biological Sciences
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Proceedings of the Japan Academy. Ser. B: Physical and Biological Sciences 98 (4), 190-205, 2022-04-11
日本学士院
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詳細情報 詳細情報について
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- CRID
- 1390854717881049088
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- NII書誌ID
- AA00785485
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- ISSN
- 13492896
- 03862208
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- HANDLE
- 2433/282797
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- NDL書誌ID
- 032124011
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- PubMed
- 35400695
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- IRDB
- NDL
- Crossref
- PubMed
- KAKEN
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- 使用不可