3 years ago

Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes

Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes
Ori Gidron, Linda J. W. Shimon, Sunita Gadakh
We demonstrate the transformation of oligofurans through sequential Diels–Alder cycloaddition reactions to provide oligoarenes in two chemical steps, regardless of the oligomer length. By this method, oligonaphthalenes containing up to six units were obtained in high yield through the formation of up to 12 new C−C bonds. The versatility of this method was demonstrated for various polyaromatic hydrocarbons. The regioselectivity of this process enabled the synthesis of a library of substituted triarylenes from a single terfuran precursor by modification of the dienophile strength and the order of addition. Overall, this study demonstrates that long oligofurans are interesting not only as organic electronic materials, but also as starting materials for the formation of various conjugated systems. To cut a long story short: Oligofurans underwent sequential Diels–Alder reactions to provide oligoarenes in two chemical steps, regardless of the oligomer length (see picture). Different maleimide and benzyne dienophiles were also used to construct a range of substituted oligoarenes from a single oligofuran precursor in a highly regioselective manner.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201705914

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