拡張Pummerer型反応を駆使したヘテロ芳香族化合物の合成

• 依光 英樹

  Graduate School of Science, Kyoto University

書誌事項

タイトル別名

• Synthesis of Heteroaromatic Compounds by Newly Extended Pummerer Reactions
• カクチョウ Pummererガタ ハンノウ オ クシ シタ ヘテロ ホウコウゾク カゴウブツ ノ ゴウセイ

抄録

Ketene dithioacetal monoxides (KDMs) bring out a variety of latent intriguing reactivity upon treatment with triflic anhydride. The extended Pummerer reactions of KDMs provide reliable accesses to heteroaromatic compounds including (benzo) furan, (benzo) thiophene, and pyrroles. Trifluoromethyl-substituted KDMs are useful building blocks to prepare α-trifluoromethyl carbonyl compounds and 3-trifluoromethyl heteroaromatic compounds. A newly uncovered interrupted Pummerer reaction/[3,3]sigmatropic rearrangement cascade is the key that realizes most of the transformations in this paper. The last part of this paper describes the first example of metal-catalyzed Pummerer reaction where sulfoxides are directly activated by the catalyst.

収録刊行物

• 有機合成化学協会誌

  有機合成化学協会誌 71 (4), 341-354, 2013

  公益社団法人 有機合成化学協会

キーワード

• Pummerer reaction
• sulfoxide
• ketene dithioacetal monoxide
• trifluoromethyl group
• furan
• pyrrole
• thiophene
• copper catalyst
• rearrangement
• migration

詳細情報

• CRID: 1390282680318185088
• NII論文ID: 130003373283
• NII論文ID: 10031165931
• NII書誌ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.71.341
• COI: 1:CAS:528:DC%2BC3sXmtVWqtrk%3D
• ISSN: 18836526
• ISSN: 00379980
• NDL書誌ID: 024631766
• Web Site: http://id.ndl.go.jp/bib/024631766
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024631766
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可