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Short Paper | Special issue | Vol 86, No. 1, 2012, pp.767-776
Published online, 17th July, 2012
DOI: 10.3987/COM-12-S(N)39
HYPERVALENT IODINE INDUCED OXIDATIVE CROSS COUPLING VIA Thiophene CATION RADICAL INTERMEDIATE

Toshifumi Dohi, Motoki Ito, Sho Sekiguchi, Yohei Ishikado, and Yasuyuki Kita*

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

Abstract

The hypervalent iodine-induced arene cross coupling via a single- electron-transfer (SET) oxidation process could proceed in some extent even in heteroaromatic compounds, that is, several types thiophenes 1, using alkyl benzenes 2 as coupling partners. The structure of the obtainable heteroaromatic biaryl products could be elaborated by utilizing the known metal-catalyzed coupling technology, i.e., Negishi cross coupling, for the synthesis of multiple arylated (bi)thiophenes.