PALLADIUM-CATALYZED HOMO-COUPLING OF HETEROARYLSULFONIUMS VIA BORYLATION/SUZUKI-MIYAURA COUPLING SEQUENCE

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...

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Bibliographic Details
Published inHeterocycles Vol. 97; no. 2; pp. 998 - 1007
Main Authors Minami, Hiroko, Nogi, Keisuke, Yorimitsu, Hideki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2018
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Summary: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.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-18-S(T)78