One-pot sequential four-component coupling via CpRuCl-catalyzed cyclotrimerization and Suzuki–Miyaura coupling

The catalytic intermolecular cyclotrimerization of alkynylboronates, propargyl alcohols, and terminal alkynes was accomplished by means of the ruthenium catalysis and the temporary tethering approach with the C–B–O linkage to give rise to highly substituted arylboronates with excellent selectivity....

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Bibliographic Details
Published in:Tetrahedron 2005-11, Vol.61 (48), p.11501-11510
Main Authors: Yamamoto, Yoshihiko, Ishii, Jun-ichi, Nishiyama, Hisao, Itoh, Kenji
Format: Article
Language:English
Subjects:
Biaryl
Cyclotrimerization
Ruthenium catalysis
Suzuki–Miyaura coupling
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Summary:The catalytic intermolecular cyclotrimerization of alkynylboronates, propargyl alcohols, and terminal alkynes was accomplished by means of the ruthenium catalysis and the temporary tethering approach with the C–B–O linkage to give rise to highly substituted arylboronates with excellent selectivity. The resultant arylboronates were further converted to highly substituted biaryls via the Suzuki–Miyaura coupling with various aryl iodides using Pd 2(dba) 3/PCy 3 as a catalyst precursor in aqueous toluene. As a consequence, the four-component coupling approach to highly substituted biaryls was successfully established by combining these two operations into a sequential one-pot process. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.08.069