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Domino Diels–Alder Cycloadditions of Arynes: New Approach to Elusive Perylene Derivatives
Author(s) -
Criado Alejandro,
Peña Diego,
Cobas Agustín,
Guitián Enrique
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001057
Subject(s) - aryne , perylene , domino , computer science , adduct , chemistry , combinatorial chemistry , organic chemistry , molecule , catalysis
A game of dominos : Domino [4+2]/[4+2] cycloadditions between 1,8‐difurylnaphthalene and arynes provide the corresponding adducts in a highly diastereoselective manner. This new synthetic methodology enables the preparation of elusive perylene derivatives with a remarkable reduced HOMO–LUMO gap, a crucial feature for organic semiconductors.