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Paper | Special issue | Vol 97, No. 2, 2018, pp.998-1007
Published online, 29th March, 2018
DOI: 10.3987/COM-18-S(T)78
Palladium-Catalyzed Homo-Coupling of Heteroarylsulfoniums via Borylation/Suzuki-Miyaura Coupling Sequence

Hiroko Minami, Keisuke Nogi, and Hideki Yorimitsu*

*Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan

Abstract

Palladium-catalyzed homo-coupling of heteroaryldimethylsulfoniums proceeds in the presence of bis(pinacolato)diboron and a base to yield biheteroaryls. The homo-coupling involves palladium-catalyzed borylation and the subsequent Suzuki-Miyaura coupling. As the sulfoniums were able to be prepared in situ from the corresponding heteroaryl sulfides and methyl triflate, one-pot transformations of heteroaryl sulfides into the homo-coupling products were executed. Furthermore, a facile synthesis of a highly substituted 2,2'-bibenzofuran was accomplished with a combination of Pummerer-type synthesis of 2-benzofuryl sulfide and the present homo-coupling.