Synthesis of ct-Amino Acid Derivatives by Insertion of Isocyanides , CO , Alkenes , and Alkynes into the PdC Bond
semanticscholar(2015)
Abstract
N,N-Dimethyl-C-phenylglycinemethylester reacts with Pd(OAc)2 in acetic acid to give the orthopalladated, acetato bridged complex 1. Treatment of 1 with sodium halide affords the chloro, bromo, and iodo bridged compounds [Me2NC(H)(C02Me)C6H4PdX]2 (2a c) (X = halide). From 2a and 1,1 '-bis(diphenylphosphino)ferrocene the phosphine bridged trinuclear complex 3 is obtained. Substitution of the amine ligand of 2a by the phosphino group is observed for the reaction of 2a with Ph2PC(Me)C(Me)PPh2. Insertion of 2,6-dimethyl-phenylisocyanide, CO, alkyl-vinyl-ketones, and diphenylacetylene into the Pd-C bond of 2a c provides the ortho substituted organic and organometallic derivatives of phenylglycine 6a c, 7, 8a b and 9a c. The crystal structures of 1, 4a, 6a, 7 and 9a were determined by X-ray diffraction.
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