HETEROCYCLES

■ Generation of Monoaryl-λ3-iodanes from Arylboron Compounds through ipso-Substitution

Ayako Nakano, Yukino Okabe, Keitaro Matsuoka, Narumi Komami, Keito Watanabe, Masahiro Kojima, Tatsuhiko Yoshino, and Shigeki Matsunaga*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-ku, Sapporo 060-0812, Japan

Abstract

Monoaryl-λ3-iodanes serve as versatile oxidants and arylating reagents in organic synthesis. In addition to the oxidation of iodoarenes, electrophilic substitution reactions using iodine tricarboxylates have been used for the synthesis of monoaryl-λ3-iodanes. Here, we report that ipso-substitution reactions of aryltrifluoroborates with iodine tris(trifluoroacetate) in DMF or DMA smoothly produced monoaryl-λ3-iodanes, which were readily converted to aryliodonium ylides. We also demonstrated that sequential C–H borylation and the ipso-substitution efficiently introduced the I(III) group under steric control.