6 (Het)Arene/Alkene Cross-Dehydrogenative Coupling for C(sp²)—C(sp²) Bond Formation

Abstract

The formation of C(sp²)—C(sp²) bonds via the coupling of an aromatic or heteroaromatic species and an alkene is of crucial importance in organic synthesis. While this responsibility has fallen mostly on the Mizoroki–Heck coupling since its discovery half a century ago, the cross-dehydrogenative counterpart, occurring from unfunctionalized reactants, has clear potential advantages in terms of synthetic flexibility and greenness. As cross-dehydrogenative couplings have attracted considerable interest in the recent past, this transformation has been developed from a very limited approach to a much more versatile method. This chapter offers an overview of the different strategies used to functionalize different classes of (hetero)aromatic species, pointing out the strengths and weaknesses of each method.

Key words

C—H functionalization - C—H activation - cross-dehydrogenative coupling - cross coupling - C—C bond formation - directing groups - transition-metal catalysis - alkenylation - olefination - Fujiwara–Moritani - arenes - heteroarenes - alkenes - olefins

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