Improvements in cross coupling reactions of hypervalent siloxane derivatives.
[formula: see text] The scope of the palladium-catalyzed cross coupling reaction of aryl halides with phenyltrimethoxysilane has been expanded to include aryl bromides, heteroaryl bromides, and aryl chlorides. A more general Pd(0)-catalyst/ligand system has been developed to activate bromides: palladium(II) acetate (Pd(OAc)2) is activated with triphenylphosphine (PPh3) or tri-o-tolylphosphine (P(o-tol)3) (1:2 molar ratio of Pd:phosphine). Coupling of aryl chloride derivatives required addition of 2-(dicyclohexylphosphino)biphenyl (Buchwald's ligand) to Pd2dba3 (tris-(dibenzylideneacetone)dipalladium(0)) (1:1.5 molar ratio of Pd:phosphine).
Mowery
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ME
Department of Chemistry and Biochemistry, University of Maryland, College Park 20742, USA.
DeShong
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P
D002384:Catalysis; D008024:Ligands; D017646:Organosilicon Compounds / Q000737:chemistry; D010165:Palladium; D012833:Siloxanes / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry
D008024:Ligands; D017646:Organosilicon Compounds; D012833:Siloxanes; D013876:Thiophenes; C410706:phenyltrimethoxysilane; D010165:Palladium