HUSCAP logo Hokkaido Univ. logo

Hokkaido University Collection of Scholarly and Academic Papers >
Faculty of Pharmaceutical Sciences >
Peer-reviewed Journal Articles, etc >

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

Files in This Item:
WoS_90277_Yoshino.pdf440.17 kBPDFView/Open
Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/79000

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)

Submitter: 吉野 達彦

Export metadata:

OAI-PMH ( junii2 , jpcoar )

MathJax is now OFF:


 

 - Hokkaido University