Chemoselective Transformations of Cyclic β-Bromoacrylic Acids with Palladacycles Formed by Aryl Iodides to Access Fused or Spiro Polycycles

A palladium-catalyzed chemoselective decarboxyla-tive annulation of different aryl iodides with cyclic beta-bromoacrylic acids for the construction of interesting fused and spiro polycycles is disclosed. Notably, cyclic beta-bromoacrylic acids can chemo-selectively act as C1 or C2 insertion units by the use of different aryl iodides. 2-Iodo-N-methacryloylbenzamides can undergo a Heck/[4+2] annulation to afford hexahydrodibenzoisoquinoline-4,6(5H)-diones. Employing 2-iodobiphenyls or N-(2-iodophenyl)-2-phenylacrylamides as substrates enables the assembly of spirofluorenes and dispirooxindoles.

Automated summary

A palladium-catalyzed chemoselective decarboxylative annulation of aryl iodides with cyclic beta-bromoacrylic acids is developed for the construction of diverse fused and spiro polycycles. The reaction exhibits high selectivity and diversity by employing different substrates.