Abstract A new, selective method for the synthesis of 4-haloisoquinolines and 3-haloindoles is presented by the halopalladation cyclizations of alkynes with azides. In the presence of PdX 2 (X= Br, Cl) and halide sources, a variety of 2-alkynyl benzyl azides or 2-alkynyl aryl azides smoothly underwent the halopalladation cyclization reaction to afford the corresponding 3-substituted 4-haloisoquinolines and 2-substituted 3-haloindoles in ...