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Synthesis of Heteroaryl Iodanes(III) via ipso-Substitution Reactions Using Iodine Triacetate Assisted by HFIP
| Title: | Synthesis of Heteroaryl Iodanes(III) via ipso-Substitution Reactions Using Iodine Triacetate Assisted by HFIP |
| Authors: | Matsuoka, Keitaro Browse this author | | Komami, Narumi Browse this author | | Kojima, Masahiro Browse this author | | Yoshino, Tatsuhiko Browse this author →KAKEN DB | | Matsunaga, Shigeki Browse this author →KAKEN DB |
| Keywords: | hypervalent compounds | | ylides | | ipso-substitution | | iodine | | stannanes |
| Issue Date: | Jul-2019 |
| Publisher: | Wiley-Blackwell |
| Journal Title: | Asian journal of organic chemistry |
| Volume: | 8 |
| Issue: | 7 |
| Start Page: | 1107 |
| End Page: | 1110 |
| Publisher DOI: | 10.1002/ajoc.201900200 |
| Abstract: | 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. |
| Rights: | This is the peer-reviewed version of the following article: Matsuoka, Keitaro, et al. / Synthesis of Heteroaryl Iodanes(III) via ipso-Substitution Reactions Using Iodine Triacetate Assisted by HFIP. Asian journal of organic Chemistry, 8(7), 1107-1110, 2019, which has been published in final form at https://doi.org/10.1002/ajoc.201900200. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/79000 |
| Appears in Collections: | 薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 吉野 達彦
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