Tetrahedron

Conjugate addition vs. vinylic substitution in palladium-catalysed reaction of aryl halides with β-substituted-α, β-enones and-enals

A Amorese, A Arcadi, E Bernocchi, S Cacchi, S Cerrini…

Index: Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; et al. Tetrahedron, 1989 , vol. 45, # 3 p. 813 - 828

Full Text: HTML

Citation Number: 75

Abstract

The reaction of β-substituted-α, β-enones and-enals with aryl halides in the presence of a palladium catalyst has been investigated. The outcome of the reaction was found to be greatly dependent on the nature of the added base. Tertiary amines tend to favour the formation of conjugate addition-type products while sodium bicarbonate or sodium acetate that of vinylic substitution products. Usually, the use of sodium acetate produced results ...

Related Articles:

A one-pot palladium-catalyzed synthesis of β, β-diarylketones and aldehydes from aryl iodides and α, β-unsaturated carbonyl compounds

[Cacchi, S.; Palmieri, G. Synthesis, 1984 , # 7 p. 575 - 577]

Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes

[Kondolff, Isabelle; Doucet, Henri; Santelli, Maurice Tetrahedron Letters, 2003 , vol. 44, # 46 p. 8487 - 8491]

Palladium-Catalyzed Oxidative Rearrangement of Diaryl Alkenyl Carbinols to β, β-Diaryl α, β-Unsaturated Ketones

[Rosa, David; Orellana, Arturo Organic Letters, 2011 , vol. 13, # 14 p. 3648 - 3651]

Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes

[Kondolff, Isabelle; Doucet, Henri; Santelli, Maurice Tetrahedron Letters, 2003 , vol. 44, # 46 p. 8487 - 8491]

Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle

[Botella, Luis; Najera, Carmen Tetrahedron Letters, 2004 , vol. 45, # 9 p. 1833 - 1836]

More Articles...