The scope of the palladium-catalyzed cross-coupling reaction of aryl bis(catechol) silicates has been extended to include the coupling of aryl bromides by employing microwave irradiation. This new set of coupling conditions is tolerant of electron-rich and -deficient aryl bromides. In addition, a variety of substituted aryl bis(catechol) silicates have been successfully cross-coupled.
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Palladium-catalyzed cross-coupling of aryl triethylammonium bis(catechol) silicates with aryl bromides using microwave irradiation.
Org Lett
November 2004
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20770, USA.
The scope of the palladium-catalyzed cross-coupling reaction of aryl bis(catechol) silicates has been extended to include the coupling of aryl bromides by employing microwave irradiation. This new set of coupling conditions is tolerant of electron-rich and -deficient aryl bromides. In addition, a variety of substituted aryl bis(catechol) silicates have been successfully cross-coupled.
View Article and Find Full Text PDFPreparation and palladium-catalyzed cross-coupling of aryl triethylammonium bis(catechol) silicates with aryl triflates.
J Org Chem
February 2004
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
Pentavalent aryl and heteroaryl bis(catechol) silicates undergo palladium-catalyzed cross-coupling with aryl and heteroaryl triflates in the presence of a fluoride source in excellent yields. These solid, air-stable bis(catechol) silicates are prepared from a high-yielding displacement reaction between catechol and an aryl siloxane in the presence of an amine base. The cross-coupling reaction is tolerant of a wide range of electron-donating and electron-withdrawing groups.
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