Metal-Catalyzed C-H Bond Activation of 5-Membered Carbocyclic Rings: A Powerful Access to Azulene, Acenaphthylene and Fulvene Derivatives

Xinzhe Shi (1) , Arpan Sasmal (1) , Jean-François Soulé (1) , Henri Doucet (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

Azulene, acenaphthylene and fulvene derivatives exhibit important physical properties useful in materials chemistry as well as valuable biological properties. Since about two decades ago, the metal-catalyzed functionalization of such compounds, via C-H bond activation of their 5-membered carbocyclic ring, proved to be a very convenient method for the synthesis of a wide variety of azulene, acenaphthylene and fulvene derivatives. For such reactions, there is no need to prefunctionalize the 5-membered carbocyclic rings. In this review, the progress in the synthesis of azulene, acenaphthylene and fulvene derivatives via metal-catalyzed C-H bond activation of their 5-membered carbocyclic ring are summarized.

Keywords: catalysis; acenaphthylenes; azulenes; C-H bond activation; fulvenes

Domains: Chemical Sciences; Organic chemistry; Chemical Sciences; Catalysis

Xinzhe Shi, Arpan Sasmal, Jean-François Soulé, Henri Doucet. Metal-Catalyzed C-H Bond Activation of 5-Membered Carbocyclic Rings: A Powerful Access to Azulene, Acenaphthylene and Fulvene Derivatives. Chemistry - An Asian Journal, 2018, 13 (2), pp.143-157. ⟨10.1002/asia.201701455⟩. ⟨hal-01709529⟩