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Contents Vol 64(5)

One-Pot Syntheses of Diaryliodonium Salts from Aryl Iodides Using Peracetic Acid as Green Oxidant

Toshifumi Dohi A , Nobutaka Yamaoka A , Itsuki Itani A and Yasuyuki Kita A B
+ Author Affiliations
- Author Affiliations

A College of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan.

B Corresponding author. Email: kita@ph.ritsumei.ac.jp

Australian Journal of Chemistry 64(5) 529-535 https://doi.org/10.1071/CH11057
Submitted: 1 February 2011  Accepted: 21 February 2011   Published: 30 May 2011

Abstract

The rate-accelerating effects of fluoroalcohol solvents for generating trivalent hypervalent iodine species and the conversion into diaryliodonium(iii) salts have been used for the first time to realize a facile and clean one-pot synthesis of diaryliodonium(iii) salts 3 from aryl iodides 1 and suitable arene partners 2 with peracetic acid (PAA). The use of PAA as a green and practical oxidant is significantly effective in fluoroalcohol solvents. The scope and limitations of the methodology are elucidated by investigation of a wide variety of representative substrates.


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