Synthesis of Heteroaromatic Compounds by Alkene and Enyne Metathesis

Abstract

The development of robust and functional group tolerant metathesis catalysts has resulted in a rapid expansion of synthetic methodologies that employ this technology. In this chapter, alkene and enyne metathesis-based methodologies for the de novo construction of heteroaromatic compounds are discussed. These protocols capitalise upon the ability to generate complex olefinic products from the combination of two simpler precursors. Advancement to the heteroaromatic target can then be achieved either directly or after modification of the immediate metathesis product. Strategies that rely upon ring-closing alkene metathesis, ring-closing enyne metathesis and alkene cross-metathesis are outlined, along with applications in target-directed synthesis.

Application of Olefin Metathesis in the Synthesis of Carbo- and Heteroaromatic Compounds—Recent Advances

“…The work of Donohoe et al [ 10 ] is an earlier review in this area. Race and Bower [ 11 ] described the state-of-the-art in the synthesis of heteroaromatic compounds by alkene and enyne metathesis up to and including 2014. An earlier review describing the possibilities offered by RCM in the synthesis of aromatic heterocycles was written by Donohoe, Fishlock, and Procopiou [ 12 ].…”