This review focuses on the regioselective metalation of condensed azoles, such as indole, indazole, benzimidazole, 4-, 5-, 6-, and 7-azaindole. The metalation strategies discussed include halogen-metal exchange, metal insertion into carbon-halogen bonds, and directed deprotonation. The influence of different nitrogenprotecting groups and directed metalating groups is discussed. This review covers literature published mainly from 1991 to 2010. 1 Introduction 2 Metalation of Indoles 2.1 C2-Metalation of Indoles 2.2 C3-Metalation of Indoles 2.3 C4-C7-Metalation of Indoles 3 Metalation of Indazoles 4 Metalation of Benzimidazoles 5 Metalation of Azaindoles 6 Conclusion