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Orthogonal reactivity in boryl-substituted organotrifluoroborates.

ABSTRACT: 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.

SUBMITTER: Molander GA

PROVIDER: S-EPMC2645949 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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Orthogonal reactivity in boryl-substituted organotrifluoroborates.

Molander Gary A GA Sandrock Deidre L DL

Journal of the American Chemical Society 20081101 47

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 fu ...[more]

PMID: 18980313

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