title: Homo- and hetero-oxidative coupling of benzyl anions.
abstract: The regioselective benzylic metalation of substituted toluenes using BuLi/KO-t-Bu/TMP(H) (LiNK metalation conditions) with subsequent in situ oxidative C-C coupling has been developed for the facile generation of 1,2-diarylethanes. A range of oxidants can be used for the oxidative coupling step, with 1,2-dibromoethane proving optimal. Heterocouplings can be achieved starting from a mixture of two different toluenes with a bias toward cross coupling achievable by using a 2-fold excess of one toluene starting material. The utility of this approach is illustrated by the synthesis of several biologically active natural products. A distinct advantage is that the synthetic steps typically required to preactivate the coupling substrates are eliminated and no transition metal is required to facilitate the C-C bond formation.
authors.affiliation: School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland.
authors.forename: Marco
authors.initials: M
authors.lastname: Blangetti
authors.forename: Patricia
authors.initials: P
authors.lastname: Fleming
authors.forename: Donal F
authors.initials: DF
authors.lastname: O'Shea