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Regioselective Transformation of Long π‐Conjugated Backbones: From Oligofurans to Oligoarenes
Author(s) -
Gadakh Sunita,
Shimon Linda J. W.,
Gidron Ori
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705914
Subject(s) - regioselectivity , conjugated system , cycloaddition , yield (engineering) , oligomer , chemistry , combinatorial chemistry , organic chemistry , materials science , polymer , catalysis , metallurgy
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.