Palladium-catalyzed successive C-H bond arylations and annulations toward the pi-extension of selenophene-containing aromatic skeletons

Xinzhe Shi (1) , Shuxin Mao (1) , Thierry Roisnel (1) , Henri Doucet (1) , Jean-François Soulé (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

A modular approach for the synthesis of planar pi-extended selenium containing molecules from selenophene has been developed. Different combinations of Pd-catalyzed desulfitative C-H bond arylations with (2-bromo)arylsulfonyl chlorides and Pd-catalyzed intra- or/and inter-molecular C-H bond arylations with aryl bromides allowed the extension of the selenophene-containing aromatic skeleton at the [b]-, [c]- or [bd]-junctions to give phenanthro[b]selenophenes, phenanthro[c]selenophenes or diphenanthro[bd]selenophenes.

Domains: Chemical Sciences

Xinzhe Shi, Shuxin Mao, Thierry Roisnel, Henri Doucet, Jean-François Soulé. Palladium-catalyzed successive C-H bond arylations and annulations toward the pi-extension of selenophene-containing aromatic skeletons. Organic Chemistry Frontiers, 2019, 6 (14), pp.2398-2403. ⟨10.1039/c9qo00218a⟩. ⟨hal-02278420⟩