RESUMO
The synthesis of substituted 2-cyanoarylboronic esters is described via lithiation/in situ trapping of the corresponding methoxy-, trifluoromethyl-, fluoro-, chloro-, and bromobenzonitriles. The crude arylboronic esters were obtained in high yields and purities and with good regioselectivities.
Assuntos
Ácidos Borônicos/síntese química , Ácidos Borônicos/química , Estrutura Molecular , EstereoisomerismoRESUMO
Ortho-substituted arylboronic esters are efficiently coupled with carbamoyl chlorides under Pd-catalysis to give tertiary benzamides.
Assuntos
Benzamidas/síntese química , Paládio/química , Carbamatos/química , Catálise , Cloretos/química , Ésteres/química , Estrutura MolecularRESUMO
[reaction: see text] The addition of organometallic derivatives to the cyano group of 2-(2-fluorophenyl)benzonitrile followed by intramolecular nucleophilic substitution produces 6-substituted phenanthridines. Alkyllithiums, aryllithiums, and sterically nondemanding lithium amides reacted at -78 degrees C to produce the 6-substituted phenanthridines in 82-98% yield upon warming to room temperature. The addition of the corresponding Grignard reagents requires an excess of the organometallic reagent and extented reaction times at elevated temperature.