Metalation of Indole

  • Erin T. PelkeyEmail author
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 26)


Metalation reactions involving indoles (and indolines) is reviewed (through 2009). The most common mode of metalation is lithiation. Other metals that have been used, either through direct metalation of indole or through transmetalation, include magnesium, zinc, tin, and boron. This monograph is divided into three sections: metalation directed by a nitrogen functionality, directed ortho metalation by substituents not located at nitrogen, and halogen–metal exchange. All of the sections are organized by the location of the metalation event. The review will have a primary focus on the seminal papers that contributed to the development of metalation reactions and a secondary focus on applications of metalation reactions used in the synthesis of complex indoles including indole natural products.


Directed ortho metalation Halogen–metal exchange Indole Lithiation 


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Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of ChemistryHobart and William Smith CollegesGenevaUSA

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