Visible-light photoredox catalysis: dehalogenation of vicinal dibromo-, α-halo-, and α,α-dibromocarbonyl compounds

Tapan Maji; Ananta Karmakar; Oliver Reiser

doi:10.1021/jo102239x

Visible-light photoredox catalysis: dehalogenation of vicinal dibromo-, α-halo-, and α,α-dibromocarbonyl compounds

J Org Chem. 2011 Jan 21;76(2):736-9. doi: 10.1021/jo102239x. Epub 2010 Dec 30.

Authors

Tapan Maji¹, Ananta Karmakar, Oliver Reiser

Affiliation

¹ Institut für Organische Chemie, Universität Regensburg Universitätsstrasse 31, 93053 Regensburg, Germany.

PMID: 21192632
DOI: 10.1021/jo102239x

Abstract

vic-Dibromo-, α-halo-, or α,α-dibromocarbonyl compounds can be efficiently dehalogenated using catalytic tris(2,2'-bipyridyl)ruthenium dichloride (Ru(bpy)(3)Cl(2)) in combination with 1,5-dimethoxynaphthalene (DMN) and ascorbate as sacrificial electron donor. For this process, a visible light promoted photocatalytic cycle is proposed that involves the reduction of carbon halogen bonds via free radical intermediates.