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Synthesis 2014; 46(14): 1933-1937
DOI: 10.1055/s-0033-1339108
DOI: 10.1055/s-0033-1339108
special topic
Copper-Catalyzed Cross-Coupling of Aryl- and Heteroaryltriethoxysilanes with Aryl and Heteroaryl Iodides and Bromides
Weitere Informationen
Publikationsverlauf
Received: 28. Februar 2014
Accepted after revision: 13. April 2014
Publikationsdatum:
28. Mai 2014 (online)
Abstract
Copper(I)-catalyzed coupling of aryl- and heteroaryltriethoxysilanes with aryl and heteroaryl iodides is described. The transformation also proceeds with activated aryl bromides, but in this case it requires a stoichiometric amount of the catalyst for best product yields. The current reaction requires a P,N-based bidentate ligand for aryl–aryl coupling while it proceeds without external ligands for aryl–heteroaryl coupling to afford good product yields. The reaction protocol can also be applied to achieve biarylation of diiodoarenes in reasonable yields.
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For selected examples of nickel-catalyzed Suzuki–Miyaura coupling, see:
For Fe-catalyzed Suzuki–Miyaura coupling, see:
Effects of copper salts on reactions involving organosilicon reagents, see:
For effects of copper salts on palladium-catalyzed Suzuki–Miyaura coupling, see:
For effects of copper salts on nickel-catalyzed Suzuki–Miyaura coupling, see:
For homocouplings of vinyl-, alkynyl-, and arylsilicon reagents with stoichiometric amounts of copper salts, see:
For a similar catalytic cycle in Ullmann amination, see: