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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Published in | Heterocycles Vol. 97; no. 2; pp. 998 - 1007 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier
2018
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Subjects | |
Online Access | Get more information |
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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. |
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ISSN: | 0385-5414 1881-0942 |
DOI: | 10.3987/COM-18-S(T)78 |