title: Highly Convergent Synthesis of Intensively Blue Emissive Furo[2,3-c]isoquinolines by a Palladium-Catalyzed Cyclization Cascade of Unsaturated Ugi Products.
abstract: A convergent and diversity-oriented approach to the unusual furo[2,3-c]isoquinoline scaffold is presented. This serendipity-driven approach is characterized by an Ugi multicomponent reaction, which gives the substrate for a palladium-catalyzed insertion-alkynylation-cycloisomerization cascade to provide the furo[2,3-c]isoquinolines in moderate to high yield. Upon UV excitation, all representatives are intensively blue luminescent, as observed by the naked eye, and quantitative fluorescence spectroscopy reveals a considerable effect of the substitution pattern on the quantum yields. The electronic structure is semiquantitatively rationalized by DFT and time-dependent DFT calculations.
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, University of Genova, Via Dodecaneso 31, 16146, Genova, Italy.
authors.forename: Lisa
authors.initials: L
authors.lastname: Moni
authors.affiliation: Institut für Organische Chemie und Makromoleculare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225, Düsseldorf, Germany.
authors.forename: Charlotte F
authors.initials: CF
authors.lastname: Gers-Panther
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, University of Genova, Via Dodecaneso 31, 16146, Genova, Italy.
authors.forename: Manuel
authors.initials: M
authors.lastname: Anselmo
authors.affiliation: Institut für Organische Chemie und Makromoleculare Chemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, 40225, Düsseldorf, Germany. ThomasJJMueller@uni-duesseldorf.de.
authors.forename: Thomas J J
authors.initials: TJ
authors.lastname: Müller
authors.affiliation: Dipartimento di Chimica e Chimica Industriale, University of Genova, Via Dodecaneso 31, 16146, Genova, Italy. renata.riva@unige.it.
authors.forename: Renata
authors.identifier: http://orcid.org/0000-0002-0829-9444
authors.initials: R
authors.lastname: Riva
keywords: Heck reaction; fluorescence; isoquinolines; multicomponent reactions; photochromism