Visible light photocatalysis of intramolecular radical cation Diels-Alder cycloadditions

TitleVisible light photocatalysis of intramolecular radical cation Diels-Alder cycloadditions
Publication TypeJournal Article
Year of Publication2012
AuthorsLin, SS, Padilla, CE, Ischay, MA, Yoon, TP
JournalTetrahedron Letters
Volume53
Pagination3073-3076
Date PublishedJun
Type of ArticleArticle
ISBN Number0040-4039
Accession NumberWOS:000304640600032
Keywords1,3-cyclohexadiene, catalysis, Diels-Alder cycloaddition, Intramolecular, Photocatalysis, electron-rich dienophiles, indole, pericyclic-reactions
Abstract

Intramolecular radical cation Die Is-Alder reactions can be conducted under photocatalytic conditions using visible light irradiation. The photocatalyst system involves the use of a Ru(bpy)(3)(2+) chromophore and methyl viologen as a co-oxidant. These reactions enable the cycloaddition of substrates whose thermal Die Is-Alder cycloadditions are electronically mismatched and thus require forcing conditions. Nevertheless, the radical cation cycloadditions can be conducted on gram scale using ambient sunlight as the only source of irradiation. (C) 2012 Elsevier Ltd. All rights reserved.

Short TitleTetrahedron Lett.