[3+2] Cycloadditions of Aryl Cyclopropyl Ketones by Visible Light Photocatalysis

Title[3+2] Cycloadditions of Aryl Cyclopropyl Ketones by Visible Light Photocatalysis
Publication TypeJournal Article
Year of Publication2011
AuthorsLu, Z, Shen, M, Yoon, TP
JournalJournal of the American Chemical Society
Volume133
Pagination1162-1164
Date PublishedFeb
Accession NumberISI:000287228500006
Keywordsaldehydes, alpha-cyclopropyl, C-h functionalization, Chemistry, Multidisciplinary, electron-transfer, enones, fragmentation-cyclization, organic-synthesis, organocatalysis, photoredox catalysis, radical-ion probes
Abstract

We report a new method for the formal [3+2] reaction of aryl cyclopropyl ketones with olefins to generate highly substituted cyclopentane ring systems. The key initiation step in this process is the one-electron reduction of the ketone to the corresponding radical anion, which is accomplished using a photocatalytic system comprising Ru(bpy)(3)(2+), La(OTf)(3), and TMEDA.

Short TitleJ. Am. Chem. Soc.