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One-Pot Synthesis of Substituted Benzo[b]furans and Indoles from Dichlorophenols/Dichloroanilines Using a Palladium-Dihydroxyterphenylphosphine Catalyst

Miyuki Yamaguchi, Tomoyo Akiyama, Hirohisa Sasou, Haruka Katsumata and Kei Manabe*

*School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan, Email: manabeu-shizuoka-ken.ac.jp

M. Yamaguchi, T. Akiyama, H. Sasou, H. Katsumata, K. Manabe, J. Org. Chem., 2016, 81, 5450-5463.

DOI: 10.1021/acs.joc.6b00824 (free Supporting Information)


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Abstract

An ortho-selective Sonogashira coupling of dichlorophenols and terminal alkynes, followed by cyclization and Suzuki-Miyaura coupling in one pot enabled the synthesis of disubstituted benzo[b]furans using a palladium-dihydroxyterphenylphosphine (Cy-DHTP) catalyst. This protocol was also successfully applied to the one-pot synthesis of disubstituted indoles from dichloroaniline derivatives.

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Key Words

Sonogashira Coupling, Suzuki Coupling, Benzofurans


ID: J42-Y2016