A convenient preparation of 4-iodoindoles from indoles: application to the chemical synthesis of hapalindole alkaloids

4-Iodoindoles were synthesized via regioselective chloromercuration and subsequent iodination of a series of N-p-toluenesulfonyl indoles bearing a variety of substituents at the 3-position This procedure allows rapid access to 3,4-dihaloindoles which may be used as synthetic precursors to indole alkaloids.