Aromatizing Route to Benzo-, Benzofuranyl-, and N-Tosylindolenyl-isoindolines

Significance

Chiral bromostyryl propargylic amines, readily prepared by the Carreira procedure (N. K. Anand, E. M. Carreira J. Am. Chem. Soc. 2001, 123, 9687-9688), undergo biscyclization, presumably through intramolecular carbopalladation and aromatic C-H insertion reactions in a one-pot process, to give benzoisoindoles (7 examples). The scope of the reaction was expanded to include the biscylization of propargylic amines incorporating bromovinyl-benzofuranyl or bromovinyl-N-tosylindolenyl units to give pyrrolidyl-annulated dibenzofuran and carbazole derivatives.