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Palladium Catalysts
No.103(July 1999)
The present reagent 1 serves as a catalyst in the reaction of aromatic halide with amine under a pressurized carbon monoxide atmosphere to form carbonyl compounds. For example, this catalyst can catalyze the reaction of o-diiodobenzene with primary amines, resulting in the formation of N-substituted phthalimides1). This catalyst tolerates a wide variety of functional groups . Formation of a wide spectrum of products in high yields is possible. In addition, it catalyzes the reaction of aromatic monohalides with secondary amines to form α-ketoamides and amides2). The α-ketoamides are useful intermediates synthesizing α-amino acids or α-hydroxycarboxylic acids.
The present reagent 2 catalyzes the coupling reaction of the organozinc reagents with aryl iodides to form the products in high yields. In the conventional method, using dichlorobis(triphenylphosphine)palladium(II) or tetrakis(triphenylphosphine)palladium(0) as a catalyst, biaryl, byproduct, are formed, but use of the present reagent 2 suppresses the formation of biaryl.
References
- 1) Preparation of N-substituted phthalimides by the Pd-catalyzed carbonylation
- 2) Pd-catalyzed double carbonylation of aryl halides
- 3) The coupling reaction of organozinc reagents with aryl iodides
- 4) Other applications
- a) 1-Alkenylation on α-position of ketones
- b) α-Phenylation of ketones
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