Electrophilic Activation of Iodonium Ylides by Halogen‐Bond‐Donor Catalysis for Cross‐Enolate Coupling

• 斎藤, 真人

  Graduate School of Pharmaceutical Sciences, Kyoto University

• 小林, 祐輔

  Graduate School of Pharmaceutical Sciences, Kyoto University

• 竹本, 佳司

  Research Initiative of Computational Sciences (RICS), Nanosystem Research Institute (NRI)・National Institute of Advanced Industrial Science and Technology (AIST)

• Takemoto, Yoshiji

  Graduate School of Pharmaceutical Sciences, Kyoto University

書誌事項

タイトル別名

• Electrophilic Activation of Iodonium Ylides by Halogen-Bond-Donor Catalysis for Cross-Enolate Coupling

抄録

The umpolung alkylation of silyl enol ethers with an iodonium(III) ylide proceeds under mild conditions to afford various 1, 4‐dicarbonyl compounds in high yields in the presence of a halogen‐bonding catalyst. Unlike typical transition‐metal activation processes of such ylide precursors, which tend to proceed via carbenoid intermediates, experimental and computational studies indicate that halogen bonding (XB) between the XB donor catalyst and the iodonium ylide plays a crucial role in promoting the reaction. The identification of a compatible Bronsted base catalyst enabled the extension of this method to enols generated in situ to give the corresponding adducts in good yields.

収録刊行物

• Angewandte Chemie

  Angewandte Chemie 56 (26), 7653-7657, 2017-06-19

  Wiley

キーワード

• organocatalyst
• umpolung
• hypervalent iodine
• XB donor

詳細情報

• CRID: 1050001338388108544
• NII論文ID: 120006653112
• NII書誌ID: AA0052535X
• ISSN: 14337851
• ISSN: 15213773
• DOI: 10.1002/anie.201703641
• HANDLE: 2433/243149
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.201703641
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.201703641
• 本文言語コード: en
• 資料種別: journal article
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