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

Organic Chemistry Frontiers Pub Date: 2019-05-16 DOI: 10.1039/C9QO00218A

Abstract

A modular approach for the synthesis of planar π-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 [b:d]-junctions to give phenanthro[b]selenophenes, phenanthro[c]selenophenes or diphenanthro[b:d]selenophenes.

Graphical abstract: Palladium-catalyzed successive C–H bond arylations and annulations toward the π-extension of selenophene-containing aromatic skeletons
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