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DOI: 10.1055/s-2002-19785
Rhodium-catalyzed Hydroarylation and -Alkenylation of Alkynes with Silanediols. A Crucial Role of the Hydroxy Group for the Catalytic Reaction
Publikationsverlauf
Publikationsdatum:
02. Februar 2007 (online)
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Abstract
Aryl- and alkenylsilanediols, which possess two hydroxy groups on the silicon atom, undergo the rhodium-catalyzed addition of an organic group on silicon to internal alkynes. Treatment of several internal alkynes with aryl- or alkenylsilanediols in the presence of 3 mol% of [Rh(OH)(cod)]2 affords the hydroarylated or hydroalkenylated products in good yields. A crucial role of the hydroxy group of silanediol for the catalytic reaction is also discussed with the related aryltin reagent.
Key words
silanediol - rhodium complex - hydroarylation - hydroalkenylation - internal alkyne
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References
All products were identical with authentic samples (ref. [4] ).
9Although Hayashi reported that 98% of alkenylrhodium rearrange to arylrhodium in the reaction of PhB(OH)2 with Rh(acac)(C2H4)2/dppb (ref. [4] ), the reaction of 2 with 1a in toluene-D2O (10:1) showed 28% deuterium incorporation at the vinylic position and 68% at the ortho position of the aromatic ring.