Oxidative Cascade Iodocyclization of 1, n -Dienes: Synthesis of Iodinated Benzo[ b ]azepine and Benzo[ b ]azocine Derivatives.

An oxidative cascade iodocyclization of 1,7- or 1,8-dienes has been realized under mild conditions. By employing I 2 as an iodine source, this protocol provides a concise and efficient approach to a great deal of biologically significant iodinated benzo[ b ]azepine and benzo[ b ]azocine derivatives in moderate to good yields. The gram-scale synthesis and further transformation of products render the approach practical and attractive. Radical trapping and deuterium-labeling experiments help to understand the mechanism.