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Palladium assisted organic reactions

1983; Elsevier BV; Volume: 253; Issue: 3 Linguagem: Inglês

10.1016/s0022-328x(00)99235-0

1872-8561

Peter W. Clark, Hazel J. Dyke, S.F. Dyke, Gregory J. P. Perry,

Asymmetric Synthesis and Catalysis

The reactions between two di-μ-chloro-bis(N,N-dialkylbenzylamine-2-C,N)dipalladium(II) complexes, and two [ethyl di-μ-chloro-bis(N-methyl-N-benzyl-2-C,N)-glycinate]dipalladium(II) complexes with a variety of acyl halides have been studied. Regiospecific ortho-acylation occurs in good to high yields in most examples. The intermediate complexes of the type [LPdCl2]2 were characterised in two cases (L = ortho-acylbenzylamine derivative). No insertion reactions were observed with (C6H5)3C·COCl or with (CH3)3C·COCl. The cyclisations of two of the ortho-acylbenzylglycinates to isoquinoline derivatives are described, to illustrate the utility of these acylation reactions in synthetic nitrogen heterocyclic chemistry.