Substituted indoles have attracted great interest over the past years due to their presence in a large number of pharmaceutical and natural products.  In one of our research projects, we became interested in the preparation of a large set of diverse 2-aryl and 2-heteroaryl substituted indoles. We devised a procedure to make the synthesis of 2-substituted indoles amenable to parallel synthesis.

This Stille coupling using a 2-stannylindole scaffold is applicable to a wide range of coupling partners. The scope and limitations of this reaction will be discussed.