Palladium-catalysed hydroarylation and hydrovinylation of 3,3-dialkoxy-1-aryl-1-propynes. An approach to 3-aryl- and 3-vinylquinolines

Article abstract of DOI:10.1016/0040-4020(96)00557-1

Acetylenic acetals and ketals have been reacted with aryl and vinyl halides to generate hydroarylation and hydrovinylation products. The reaction proceeds with high regioselectivity. The carbopalladation step appears to be mainly controlled by steric effects and the new carbon-carbon bond is generated preferentially on the carbon bearing the acetal group. The reaction has been employed to develop a regioselective synthesis of 3-aryl and 3-vinylquinolines.