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Short Paper | Special issue | Vol 95, No. 2, 2017, pp.1272-1284
Published online, 17th February, 2017
DOI: 10.3987/COM-16-S(S)90
Selective Aryl Radical Transfers into N-Heteroaromatics from Diaryliodonoium Salts with Trimethoxybenzene Auxiliary

Toshifumi Dohi, Shohei Ueda, Akiko Hirai, Yusuke Kojima, Koji Morimoto, and Yasuyuki Kita*

*Research Organization of Science and Technology, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan


We have found that a series of trimethoxybenzene-based diaryliodonium(III) salts I (ArI+Ar’X-, where Ar = various aryl groups, Ar’ = 2,4,6-trimethoxyphenyl, X- = counterion) can exclusively cause Ar-transfers during the base-induced radical couplings with N-heteroaromatic compounds 1 by working the trimethoxybenzene ring (Ar’) as an inert coupling auxiliary. By the treatment with N-heteroaromatics 1 as the solvent, the metal-free arylations utilizing the specific salts I initiated by solid NaOH upon heating selectively produced the corresponding biaryls 2 in good yields without the formation of the trimethoxybenzene (Ar’) coupling product.