Reactions of Indoles with Metal-Bound Carbenoids

Abstract Indoles are a broadly occurring functional group in nature and are found in an expansive number of bioactive natural products and pharmaceutical compounds. As such, there has been a growing interest in the development of novel methods for site-selective functionalization of the indole core. This review will focus on the inter- and intramolecular reactions of indoles with metal-bound carbenoids, including cyclopropanation, alkylation, and annulation reactions, as well as the growing number of asymmetric variants of these transformations. In addition, the applications of these transformations to the syntheses of a number of indole-containing natural products will be discussed.