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Review | Regular issue | Vol 94, No. 12, 2017, pp.2179-2207
Published online, 4th October, 2017
DOI: 10.3987/REV-17-869
■ Synthesis of Unsymmetric HetAr–X–HetAr’ Compounds by Rhodium-Catalyzed Heteroaryl Exchange Reactions

Mieko Arisawa,* Saori Tanii, Takeru Tazawa, and Masahiko Yamaguchi*

*Graduate School of Pharmaceutical Sciences, Tohoku University, Aramaki, Aoba-ku, sendai 980-8578, Japan

Abstract

Unsymmetric HetAr-X-HetAr’ compounds have flexible and chiral structures, and are expected to exhibit various biological activities by interacting with proteins and nucleic acids. Unsymmetric HetAr-X-HetAr’ compounds were efficiently synthesized by rhodium-catalyzed heteroaryl exchange reactions, which involved equilibrium control by judicious design of organic heteroaryl reagents. By using this method, unsymmetric HetAr–O–HetAr’, HetAr–S–HetAr’, and HetAr–CH2–HetAr’ compounds as well as HetAr–F compounds were obtained from heteroaryl aryl ethers and various heteroaryl reagents. The rhodium-catalyzed synthesis has a broad applicability, which gives novel unsymmetric HetAr-X-HetAr’ compounds containing five- and six-membered heteroarenes.