希土類およびハフニウムトリフラートを用いたカルボカチオン生成と各種求核試薬との反応

• 野地 匡裕

  明治薬科大学

• 石井 啓太郎

書誌事項

タイトル別名

• Rare Earth Metal and Hafnium Triflate-catalyzed Generation of Carbocation and Reaction with Various Nucleophiles
• キドルイ オヨビ ハフニウム トリフラート オ モチイタ カルボカチオン セイセイ ト カクシュ キュウカク シヤク トノ ハンノウ

抄録

The rare earth metal and hafnium triflate-catalyzed cationic benzylation of various nucleophiles using benzylic alcohols is described. The reaction of benzylic alcohols with aromatic compounds in nitromethane in the presence of catalytic amount of metal triflate gave Friedel-Crafts-type benzylation products in high yield. Direct use of the alcohol as a source of an electrophile produces only water as a side product. Water-tolerant rare-earth metal triflates effectively catalyzed the alkylation under non-anhydrous conditions and the catalysts could be reused up to three times. The benzylation system also showed compatibility over a wide range of nucleophiles such as olefin, allylsilane, enol acetates, diketones, ketoesters, alcohols, and amides. The reaction conditions of various combinations of benzylic alcohols and nucleophiles were easily optimized by the two-dimensional catalysts-temperature screenings using La, Yb, Sc, and Hf triflates.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 67 (2), 114-122, 2009

  公益社団法人 有機合成化学協会

キーワード

• rare earth metal triflate
• hafnium triflate
• benzylic alcohol
• benzylic cation
• Friedel-Crafts alkylation
• enol acetate
• dicarbonyl compounds

詳細情報

• CRID: 1390001205311463296
• NII論文ID: 10024967503
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.67.114
• COI: 1:CAS:528:DC%2BD1MXhvFWjtL0%3D
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 10165256
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10165256
• 本文言語コード: ja
• データソース種別:
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  • NDL
  • Crossref
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  • KAKEN
• 抄録ライセンスフラグ: 使用不可