Synthesis of Heteroaryl Iodanes(III) via <i>ipso</i>‐Substitution Reactions Using Iodine Triacetate Assisted by HFIP

• Matsuoka, Keitaro

• Komami, Narumi

• Kojima, Masahiro

• Yoshino, Tatsuhiko

• Matsunaga, Shigeki

書誌事項

タイトル別名

• Synthesis of Heteroaryl Iodanes(III) via ipso-Substitution Reactions Using Iodine Triacetate Assisted by HFIP

抄録

The synthesis of monoaryl-lambda(3)-iodanes generally requires the oxidation of iodoarenes, but the functional group compatibility is often problematic when using oxidizable substrates such as heteroaromatic compounds. Although electrophilic aromatic substitution or ipso-substitution reactions using iodine tricarboxylates have been studied as an alternative synthetic route to dicarboxyiodoarenes, several common heteroaromatic substrates such as indoles, quinolines, (benzo)furans, and (benzo)thiophenes have not been investigated to date. Here, we report that ipso-substitution reactions of heteroaromatic stannanes using I(OAc)(3) in the presence of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) effectively provide diacetoxyiodoarenes, which can be converted into the corresponding iodonium ylides or be directly used in a one-pot iodoarylation reaction.

収録刊行物

• Asian journal of organic chemistry

  Asian journal of organic chemistry 8 (7), 1107-1110, 2019-07

  Wiley-Blackwell

キーワード

• hypervalent compounds
• ylides
• ipso-substitution
• iodine
• stannanes

詳細情報

• CRID: 1050003824926920576
• NII論文ID: 120006876285
• DOI: 10.1002/ajoc.201900200
• ISSN: 21935815
• ISSN: 21935807
• HANDLE: 2115/79000
• Web Site: https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fajoc.201900200
• Web Site: https://onlinelibrary.wiley.com/doi/pdf/10.1002/ajoc.201900200
• Web Site: https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ajoc.201900200
• 本文言語コード: en
• 資料種別: journal article
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