Straightforward and rapid access to 2-arylbenzo [b] thiophenes has been developed. It involved a catalytic coupling of 3-activated benzo [b] thiophenes with several aryl halides in the presence of a phosphine-free palladium system. In case of fragile functional groups such as aldehydes, a quaternary ammonium was used as an additive as with the other substrates, the coupling performed better and faster in the presence of a crown ether, the best one ...
[Acheson, R. Morrin; Cooper, Martin W. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980 , p. 1185 - 1193]