2.8 Iron-Catalyzed C—H Functionalization

Abstract

The direct functionalization of an organic substrate via transition-metal-catalyzed C—H bond activation is a powerful tool for building molecular complexity. Despite the abundance, low cost, and low toxicity of iron, which make it an ideal metal for sustainable catalysis, iron-catalyzed C—H activation has been less investigated compared with catalysis based on precious metals such as palladium or iridium. In this chapter, selected examples of iron-catalyzed activation of a C—H bond to create a new C—C bond are described. Arylation, hetarylation, alkenylation, and alkylation of C(sp²)—H and C(sp³)—H bonds is discussed. Most of the substrates require a directing group, but several examples of non-directed reactions are also presented. The functionalization of a C—H bond has been achieved by using organometallic reagents, organic halides and pseudohalides, multiple bonds such as alkenes and alkynes, and arenes or hetarenes as the reaction partner.

Key words

C—H activation - C—H functionalization - C—C bond formation - iron catalysis - arylation - alkenylation - alkylation - directing group - bipyridine ligands - phosphine ligands - NHC ligands - organometallic reagents - alkyl halides - alkenes - alkynes - arenes - hetarenes

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