Radical-Nucleophilic Aromatic Substitution

ROSSI, R. A.; GUASTAVINO, J. F.; BUDÉN, M. E.

Arene Chemistry: Reaction Mechanisms and Methods for Aromatic Compounds

John Wiley and Sons, Inc.

Lugar: Hoboken, NJ 07030; Año: 2015; p. 243 - 268

Since its discovery, the radical-nucleophilic substitution (SRN1) reaction has been widely used to achieve new C?C or C?heteroatom bonds. The mechanism involves a chain propagation cycle with radicals and radical anions as intermediates. Here, we will discuss the SRN1 reactions of aromatic substrates with carbanions and heteroaromatic nucleophiles as well as the ring closure reactions to obtain heterocycles. Every year, new synthetic strategies and mechanistic studies involving SRN1 reactions are reported, which constitute a useful tool in the field of organic chemistry. In this chapter, we will describe the most recent advances in SRN1 reactions. With this aim in mind, we expect to cover recent SRN1 substitutions, with an emphasis on the scope of the process in terms of synthetic capability and target applications