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Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates

2008; American Chemical Society; Volume: 130; Issue: 47 Linguagem: Inglês

10.1021/ja807076d

1943-2984

Gary A. Molander, Deidre L. Sandrock,

Radical Photochemical Reactions

A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.