A selective and tin-free Pd-catalyzed phenylselenylation of aryl bromides

Article type: Research Article

Authors: Cho, Joon Hyung | Brown, Fallon V. | Shaughnessy, Kevin H.

Affiliations: Department of Chemistry, The University of Alabama, Tuscaloosa, AL, USA

Note: [] Corresponding author. E-mail: [email protected]

Abstract: The first selective palladium-catalyzed phenylselenylation of aryl bromides using a tin-free phenylselenolate source is reported. High selectivity for the desired asymmetric diaryl selenide is achieved using a catalyst derived from palladium and a Josiphos-type ligand with (PhSe)2/NaBH4 as the phenylselenylating agent. Aryl bromides are phenylselenylated at 100°C using low catalyst loadings to give the desired asymmetric diaryl selenides in high yield and >95% selectivity. Phenylselenoborane adducts formed by the reduction of diphenyl diselenide with sodium borohydride are more selective phenylselenylating reagents than sodium phenylselenolate.

Keywords: diaryl selenide, diphenyl diselenide, palladium catalyst, Josiphos ligand, cross-coupling

DOI: 10.1080/10241220801967367

Journal: Main Group Chemistry, vol. 6, no. 3, 4, pp. 201-214, 2007