Pyrroles and indoles are important subunits of many natural products and pharmacologically active compounds. Fluorinated compounds possess a unique complex of physical, chemical, and biological properties that results in their wide application as construction materials, liquid crystalline materials, agrochemicals, and drugs. The review covers the synthesis and properties of fluoropyrroles and their benzo analogues. The literature up to 2011 is highlighted. 1 Introduction 2 Synthesis of Fluoropyrroles 2.1 Functionalization of the Pyrrole Ring 2.2 Cycloaddition and Heterocyclization 2.3 Other Methods 3 Synthesis of Indoles, Indolizines and Deazopurines with Fluorinated Pyrrole Rings 3.1 Functionalization of the Pyrrole Ring 3.2 Heterocyclizations 4 Synthesis of Indoles with Fluorine Atoms on the Carbocycle 5 Properties of Fluorinated Pyrroles and Indoles 6 Conclusions