RESUMO
Herein, a new copper-catalysed strategy for the synthesis of rare nitrogen-linked seven-, eight- and nine-membered biaryl ring systems is described. It is proposed that the reaction proceeds through a highly activated intramolecularly co-ordinated copper catalyst. The process is technically simple, proceeds under relatively mild conditions, displays a broad substrate scope and forms biologically valuable products that are difficult to synthesise by other methods. We envisage that this methodology will prove useful in a wide synthetic context, with possible applications in both target-oriented and diversity-oriented synthesis.
Assuntos
Antibacterianos/síntese química , Cobre/química , Compostos Heterocíclicos/síntese química , Nitrogênio/química , Antibacterianos/química , Antibacterianos/farmacologia , Catálise , Chromobacterium/efeitos dos fármacos , Técnicas de Química Combinatória , Ciclização , Escherichia coli/efeitos dos fármacos , Compostos Heterocíclicos/química , Compostos Heterocíclicos/farmacologia , Testes de Sensibilidade Microbiana , Estrutura Molecular , Staphylococcus aureus/efeitos dos fármacosRESUMO
The regio- and stereoselective synthesis and subsequent Hiyama cross coupling of pentafluorophenyldimethylvinylsilanes has been developed, thus providing a convenient and robust method for the diversity-oriented synthesis of (E)-, (Z)- and alpha-disubstituted alkenes from terminal alkynes. Pentafluorophenyldimethylvinylsilanes undergo cross-coupling reactions with excellent selectivity and in good yields, offering an attractive alternative to existing masked silanols.
Assuntos
Alcenos/síntese química , Alcinos/química , Silanos/química , Alcenos/química , Catálise , Técnicas de Química Combinatória , Hidrocarbonetos Fluorados/síntese química , Hidrocarbonetos Fluorados/química , Estrutura Molecular , Silanos/síntese química , EstereoisomerismoRESUMO
A wide range of organozinc substrates may be oxidized in the presence of catalytic copper to give carbon-carbon bonds in high yield.