Rapid access to dibenzohelicenes and their functionalized derivatives

Angew Chem Int Ed Engl. 2013 Sep 16;52(38):9970-5. doi: 10.1002/anie.201301739. Epub 2013 Aug 9.

Abstract

Spiraling up: Easy access to dibenzo[5]-, dibenzo[6]-, and dibenzo[7]helicenes as well as their functionalized derivatives includes Sonogashira and Suzuki-Miyaura couplings, desilylation, and [2+2+2] alkyne cycloisomerization. The simplicity of this non-photochemical approach combined with the potential for helicity control favors dibenzohelicenes over the parent helicenes for practical applications.

Keywords: alkynes; aromaticity; asymmetric synthesis; chirality; helical structures.